Another option worth considering is the TaxAct DeductionPro feature, which I switched to after hearing about ItsDeductable's discontinuation. It's similar to what others mentioned about H&R Block and TaxSlayer, but I found their valuation database to be really comprehensive - especially for electronics and household appliances that can be tricky to value. The nice thing about TaxAct is that you can use their donation tracker year-round even if you don't file your taxes through them. They pull valuation data from multiple sources including thrift store guides, so the suggested values tend to be well within IRS-acceptable ranges. I've been testing it alongside the Salvation Army guide for the past month, and the values are usually within 10-15% of each other, which gives me confidence I'm in the right ballpark. Plus it has a mobile app that lets you scan receipts directly, though I still take photos of the actual items like some others mentioned here for my own records. For anyone donating regularly like the original poster, having a system that can handle both receipt scanning AND provide reliable valuations is really helpful for staying organized throughout the year.

Thanks for the reality check @Un Tyming - you're absolutely right about those details. I got confused between the different tax software features and made some inaccurate claims about year-round access. This actually highlights why it's so frustrating that ItsDeductable is going away. Most of these tax software "solutions" are really just tools you can use during tax season when you're already committed to their platform, not the kind of ongoing donation tracking system that ItsDeductable provided throughout the year. It sounds like the standalone solutions (like that taxr.ai service Jacob mentioned, or the DIY spreadsheet approach with Salvation Army/Goodwill guides) might be the better alternatives for people who want to track donations as they happen rather than trying to reconstruct everything at tax time. Has anyone found other tools that actually work year-round for donation tracking without being tied to a specific tax prep service? The whole point was having something readily available whenever I'm dropping off donations, not just in March when I'm doing my taxes.

A little warning from someone who messed this up before - make absolutely sure your total family contributions don't exceed the correct limit! I incorrectly thought my wife and I could each contribute the family maximum to our separate HSAs, and ended up with an excess contribution. The IRS charged me a 6% excise tax on the excess amount for each year it remained in the account. Had to file Form 5329 and everything. What a nightmare! To recap what others have said: - Family limit for 2025: $9,750 - Catch-up contribution if 55+: $1,000 per eligible person - Each catch-up must go to separate HSA owned by that person - Total max for married couple both 55+: $11,750

Great question! I went through this exact same confusion last year. Yes, you can absolutely add both catch-up contributions for a total of $11,750 since you're both over 55. However, there's one critical detail that trips up a lot of people (including me initially): your wife will need her own separate HSA account for her $1,000 catch-up contribution. Here's how it breaks down: - Base family contribution: $9,750 (can go into either HSA or split between them) - Your catch-up: $1,000 (must go into your HSA) - Wife's catch-up: $1,000 (must go into an HSA in her name) The catch-up contributions are tied to the individual, not the family plan. So even though you have family coverage, each person's catch-up must go into their own HSA account. If your current HSA is only in your name, you'll need to open a second HSA for your wife to receive her catch-up contribution. This is actually a pretty common misconception, so don't feel bad about being confused! The important thing is getting it right before you make the contributions to avoid any excess contribution penalties.

Did you check your transcript on the IRS website? Sometimes that gives more detailed info than the "Where's My Refund" tool. You might see codes there that explain why your TAX refund is delayed. You'll need to create an account if you don't already have one.

I'm dealing with the exact same situation! Filed on January 20th and still showing "being processed" after almost a month. What's really frustrating is that I have friends who filed later than me and already got their TAX refunds. One thing I learned from calling my tax preparer is that even though we think our returns are "simple," sometimes there are automatic reviews that we don't know about. For example, if your refund amount is significantly different from last year, or if there are any slight mismatches in the data the IRS has on file vs what you reported, it can trigger a review. The good news is that February is historically the worst month for processing times. Once we get into March, things typically speed up a lot. I'm trying to be patient but it's hard when you're counting on that money!

Something else to consider - if you revert back to LLC status, make sure you understand how it affects your self-employment taxes. When you had S-Corp status, you were probably taking a reasonable salary and then distributions that weren't subject to SE tax. Once you switch back to partnership taxation (assuming multi-member LLC), all your distributive share of income will typically be subject to self-employment tax, not just the salary portion. This can be a significant increase in your overall tax burden depending on your income levels. We made this switch last year and our overall tax bill went up about $12,000 because of the SE tax difference, even though it was still the right move for other reasons.

I just went through this exact process last month and wanted to share some key timing considerations that weren't mentioned yet. When you file your S-Corp revocation letter, make sure to specify that it's effective as of January 1, 2025 (beginning of the tax year) rather than the date you submit the letter. This ensures clean tax reporting for the entire year. Also, don't forget about estimated tax payments. Since you'll be switching from corporate taxation back to pass-through taxation, your quarterly estimated tax obligations will change significantly. We had to recalculate our safe harbor payments and adjust our Q1 2025 estimated taxes to account for the different tax structure. One more thing - if you have any outstanding payroll liabilities or employment tax deposits as an S-Corp, make sure those are fully resolved before making the switch. The IRS can get confused about which entity is responsible for what if there are any loose ends during the transition period.

I appreciate all the detailed responses here! This is exactly the kind of guidance I was hoping for. It sounds like the consensus is that gift cards will be taxable regardless of how we structure it. I'm leaning toward the suggestion to redeem points for actual merchandise instead of gift cards to potentially qualify for de minimis treatment. I'll check our credit card portal to see what options are available under $75 per person. The board approval point is really important too - I hadn't thought about the private benefit implications. I'll make sure we document everything properly and get board approval before proceeding with any approach. Thanks everyone for helping me think through all these angles. Better to handle this correctly from the start than deal with IRS issues later!

Another approach to consider is timing the gift-giving strategically. If you're committed to using gift cards, you might want to spread them across tax years or combine them with other compensation adjustments. For instance, if you were planning year-end bonuses anyway, you could reduce the cash bonus slightly and add the gift card value, then gross up the total to cover taxes. This way employees still get the same net benefit, but you're being completely transparent about the tax treatment. Also worth noting - some credit cards allow you to transfer points to travel partners or other loyalty programs. If any of your employees travel for work, you might be able to redeem points for travel credits that could qualify as working condition fringe benefits rather than taxable income, though this gets pretty complex and would definitely need professional tax advice to structure properly. The key is being upfront with everyone about the tax implications rather than trying to find workarounds that might not hold up under IRS scrutiny.