Best tax software for calculating hypothetical tax returns & comparing different scenarios

Does TaxCaster actually let you see how specific deductions affect things? Last time I used it, it was pretty basic. Any other options that are more detailed but still user-friendly?

TaxCaster is definitely more basic - good for quick estimates but not detailed deduction analysis. For more detailed scenarios, I recommend actually starting a return in the full TurboTax or H&R Block software where you can save different versions. Most tax software has a "forms mode" that lets you directly manipulate specific entries on tax forms and immediately see the impact on your return. This gives you the granular control to test specific deductions while keeping everything else constant.

Does it work if I'm self-employed with 1099 income? Most tax calculators seem designed for W-2 employees and don't handle self-employment taxes well.

Sounds interesting, but can it handle complex situations like rental properties or stock sales with different cost basis scenarios? I need something that can handle capital gains calculations too.

It absolutely handles 1099 income and self-employment taxes - that's actually what I was using it for. It lets you compare scenarios with different business deductions and shows how they affect both income tax and self-employment tax. For complex situations like rental properties and stock sales, it handles those too. You can input different scenarios for capital gains (short vs long-term) and see how various selling strategies would affect your tax liability. It even shows the tax bracket implications of each decision.

Wait, how does this work? You pay a service to call the IRS for you? Couldn't you just keep calling yourself?

Yeah right. No way this actually works. I've tried calling the IRS dozens of times and always get the "we're experiencing high call volume" message. I seriously doubt any service can magically get through when millions of people can't.

It doesn't call for you - it uses technology to navigate the IRS phone system and secures your place in line. When you're about to be connected, you get a call to join. No more waiting on hold for hours or getting disconnected. I was super skeptical too at first. But after trying for literally weeks to get through on my own with no success, I was desperate. The difference is they have systems that can stay on hold indefinitely and know exactly when to call for shortest wait times. I got through in 37 minutes when I'd previously wasted hours getting nowhere.

Does FreeTaxUSA have a good interface for comparing the scenarios side by side? That's what I'm really looking for - being able to see exactly what changes between different filing situations without having to flip back and forth between returns.

It doesn't have a dedicated comparison feature, but I create spreadsheets to track the differences when I run multiple scenarios. What I do is complete a baseline return first, then duplicate it and make my changes, noting the differences in refund/amount owed. FreeTaxUSA is much more detailed than the free calculators, so you can test specific deductions and credits. The lack of a built-in comparison tool is the only downside, but the price difference compared to TurboTax makes it worth the extra step of tracking changes manually.

That estimator is only for figuring out W-4 withholding, not really for comparing different deduction scenarios or filing statuses. It's super limited.

This DIY spreadsheet approach is really intriguing! I'm pretty comfortable with Excel, and I like the idea of having complete control over the calculations. Do you happen to have any tips for where to find the most up-to-date tax tables and formulas? I want to make sure I'm using the correct brackets and phase-out ranges for 2024. Also, when you built yours to handle student loan payment impacts, did you include the formula for how AGI affects income-driven repayment amounts? That's a huge factor for us since my partner has significant student loans, and I'm worried that getting married could dramatically increase their monthly payments even if we save on taxes overall. Would you be willing to share any resources or templates you found helpful when setting this up? Even just knowing which IRS publications have the cleanest data would be super helpful!

I'd be happy to share some resources! For the most current tax info, I pull data directly from IRS Publication 15 (Circular E) and Publication 17 - they're updated annually and have all the brackets, standard deductions, and phase-out ranges in clean tables that are easy to reference in formulas. For student loan payment calculations, yes, I built in the IDR formulas! The key is that most income-driven plans use 10-15% of your "discretionary income" (AGI minus 150% of poverty guidelines). Getting married can be brutal here because your spouse's income counts toward AGI even if they don't have loans. I've seen couples where marriage saves $2,000 in taxes but increases loan payments by $300/month - definitely not worth it financially. The Department of Education's Federal Student Aid website has the exact formulas for each IDR plan type. What I do is create scenarios with both current AGI and projected married AGI, then calculate the annual difference in loan payments and subtract that from any tax savings to get the "true" financial impact of marriage. I can put together a basic template with the 2024 tax brackets and IDR formulas if you're interested - would just need to clean up my personal info from the version I use. The setup takes a weekend but then you have complete control over modeling any scenario you can think of!

I'd be happy to share some resources! For the most current tax info, I pull directly from IRS Publication 15 for withholding tables and Publication 17 for individual tax guidance. The IRS website also has downloadable Excel versions of the tax tables at irs.gov/pub/irs-pdf/ - just search for the current year's forms. For student loan payment calculations, yes I built in the IDR formulas! The key is that most income-driven plans use 10-15% of "discretionary income" which is AGI minus 150% of the federal poverty guideline for your household size. So marriage can definitely spike payments if it pushes you into higher AGI brackets, even if your actual tax liability goes down. I actually created a template that handles both the tax calculations and student loan payment impacts side-by-side. The marriage penalty analysis gets really interesting when you factor in both! Would you like me to share the basic structure? It's not too complex once you break down the formulas, and having everything in one place makes it much easier to see the total financial impact of different decisions rather than just looking at taxes in isolation.

I'd be happy to share some resources! For the most current tax tables, I always go straight to IRS Publication 15 (Employer's Tax Guide) and Publication 17 (Your Federal Income Tax) - they have the cleanest, most organized bracket information. The IRS also publishes annual updates to the standard deductions and phase-out ranges in their "Revenue Procedures" which you can find on irs.gov. For student loan payment calculations, yes, I built in the income-driven repayment formulas! The key is that most IDR plans use your "discretionary income" which is your AGI minus 150% of the federal poverty guideline for your household size. For married couples, this gets tricky because filing jointly combines your incomes but filing separately might limit certain tax benefits. Here's what I'd suggest: model three scenarios for the student loans - 1) both single (current payments), 2) married filing jointly (combined AGI affects payments), and 3) married filing separately (only borrower's income counts but you might lose tax benefits). The third option is often overlooked but can sometimes keep loan payments manageable. I don't have a template I can share directly, but the Federal Student Aid website has the exact IDR calculation formulas, and combining those with the IRS tax tables gives you everything you need. The math isn't too complex once you break it down step by step!

I'd be happy to share some resources! For the most current tax tables, I always start with IRS Publication 15 (Circular E) and Publication 17 - they have the cleanest data in spreadsheet-friendly formats. The IRS website also has downloadable Excel files with tax brackets that you can directly import. For student loan payment calculations, yes, I built in the IDR formulas! The key insight is that married filing jointly uses combined AGI for student loan calculations even if only one spouse has loans. So you might save $2,000 on taxes but see loan payments increase by $300/month - that's $3,600 annually, making marriage a net loss financially. The formula for IDR payments is generally 10% of discretionary income (AGI minus 150% of poverty guideline for your household size). I can share my template structure if you're interested - it's set up to automatically calculate both the tax impact and loan payment changes for different filing scenarios. The intersection of these two calculations is where the real insights happen for couples with student debt. Feel free to DM me if you want the specific cell formulas - happy to help a fellow Excel enthusiast avoid the expensive software route!

Absolutely! For the most current tax data, I pull directly from IRS Publication 15 (for withholding tables) and Publication 17 (for individual tax info). The IRS website also has clean CSV downloads of the tax brackets under their "Tax Statistics" section - much easier than trying to copy/paste from PDFs. For student loan payments, yes - I included the income-driven repayment formulas! The key is that most IDR plans use "discretionary income" which is AGI minus 150% of the poverty guideline for your family size. When you get married, your family size increases but so does the income calculation if you file jointly. The formula is roughly: (Joint AGI - Poverty Threshold) × 10% (for SAVE plan) or 15% (for IBR) divided by 12 for monthly payment. I'll send you my template - it includes tabs for federal taxes, state taxes (you'd need to adjust for your states), and loan payment calculations. The student loan impact piece has been eye-opening for several friends who used it. In some cases, the marriage penalty from increased loan payments actually outweighed the tax savings! One heads up: make sure to model both "married filing jointly" AND "married filing separately" for the loan calculations, since some IDR plans let you use just your individual income even when married if you file separately.

I'd be happy to share some resources! For the most current tax tables, I always go straight to IRS Publication 15 (Circular E) for withholding tables and Publication 17 for the tax brackets and standard deductions. The IRS website also has a "Tax Tables" section under Forms & Instructions that gets updated annually. For student loan payment calculations, yes - I built in the IDR formulas from the Federal Student Aid website. The basic formula is (AGI - 150% of poverty guideline for your family size) × payment percentage (usually 10% for most IDR plans). But here's the key thing: once you're married, your spouse's income counts toward AGI even if they don't have loans, which can dramatically increase payments. I actually created a "marriage impact calculator" section that shows both the tax savings AND the student loan payment increase side by side. In many cases, the loan payment increase can completely wipe out tax savings - definitely something to factor into your decision timeline. I can share a template, but honestly, starting with the IRS Interactive Tax Assistant might be easier for getting the basic structure right before customizing. They have a tool that walks through the calculations step by step. Would be happy to help troubleshoot specific formula questions if you decide to go the DIY route!

Absolutely! For the most current tax tables, I always go straight to IRS Publication 15 for withholding tables and the Form 1040 instructions for the current year's brackets and standard deductions. The IRS website has a "Forms and Instructions" section that's updated annually - just search for "2024 tax tables" or whatever year you're planning for. For student loan payment calculations, yes, I did build in the IDR formulas! The key is that most income-driven plans use 10-15% of discretionary income (AGI minus 150% of poverty guidelines for your family size). Getting married can be brutal if both spouses have decent incomes because it combines your AGI for the calculation even if you file taxes separately. I'd be happy to share my basic template structure - I can't share the actual file due to personal info, but I can walk you through the key formulas and cell references I used. The trickiest part is handling the tax bracket calculations correctly, but once you get the nested IF statements right, it's pretty straightforward to modify for different scenarios. Want me to post the basic formula structures here, or would you prefer I point you toward some IRS resources to build your own from scratch?