Has anyone considered the option of an intra-family mortgage instead? My brother loaned me $175k to buy my house and we used a service to create a legally binding mortgage with him as the lender. I got a lower rate than the bank offered, he got better returns than his savings account, and everything is properly documented for tax purposes. The advantage is that everything is clearly aboveboard with the IRS since it's structured as a traditional mortgage, just with a family member as the lender. I can even deduct the mortgage interest I pay him, and he reports the interest as income. Might be cleaner than the HELOC arrangement.

One thing to keep in mind is that if your parents take out a HELOC or mortgage in their names but you're making the payments, you'll want to make sure the loan agreement doesn't prohibit this arrangement. Some lenders have clauses about the borrower being the actual user of funds. Also, consider the liability aspect - if something happens and you can't make the payments, your parents are still legally responsible for the debt. This could put their home at risk. You might want to explore getting life insurance or disability insurance to protect them in case you become unable to pay. From a practical standpoint, you'll need to set up a system where you can reliably make the payments directly to the lender or reimburse your parents immediately. Any delays could affect their credit score since they're the official borrowers. Having a separate account dedicated to these payments might help keep everything organized and documented for tax purposes.

Don't overthink this! Just split the difference by claiming "single, 0 dependents" on both jobs and adding extra withholding on the higher paying job. I did this for years and it worked fine. The tax brackets jump pretty significantly around 100k so having both jobs pushes you into higher rates that neither job accounts for alone.

I went through this exact same situation last year with two jobs totaling around $140k, and I can definitely relate to the stress! Here's what worked for me: The key thing to understand is that each employer calculates withholding as if their job is your only income. So with $73k + $64k, you're actually in a much higher tax bracket than either employer realizes. I ended up using the IRS Tax Withholding Estimator (it's free on irs.gov) and it was actually pretty accurate despite seeming complicated at first. For your income level, you'll likely need to have additional withholding from one job - probably around $400-500 per month based on my experience. In ADP and Workday, look for these sections: - Step 2(c): Check the "Multiple Jobs" box on BOTH forms - Step 4(c): Add the extra withholding amount on your HIGHER paying job only Don't add extra withholding to both jobs or you'll way overwithhold. I made that mistake initially and got a huge refund, which isn't ideal either. If the online tools are still confusing, honestly your HR departments should be able to help you navigate their specific systems. Most have dealt with this before since multiple jobs are pretty common now. You've got this! Better to figure it out now than get surprised at tax time.

This thread has been incredibly helpful - I'm dealing with a similar situation where my rental property was destroyed in a wildfire two years ago. Insurance covered the mortgage, but I've been holding onto the vacant land ever since. One thing I'd add that might be relevant for @fd802658100b and others: if you're planning to sell in the next year or two, consider whether you have any other investments that might generate capital losses. I discovered I had some underperforming stocks that I was planning to sell anyway - by timing both sales in the same tax year, I was able to offset a significant portion of my land sale gains with those losses. Also, don't forget about the Net Investment Income Tax (NIIT) if your modified adjusted gross income is above certain thresholds ($200K single/$250K married filing jointly). This adds an additional 3.8% tax on investment income, including capital gains from land sales. It's something that caught me off guard when I was initially calculating my potential tax liability. The advice about gathering documentation early is spot on. I spent weeks trying to reconstruct my basis calculation because I couldn't find my original property tax assessments. Your county assessor's office should have historical records, but getting them can take time, especially if the fire destroyed local government offices too.

This has been such a comprehensive discussion - I'm really grateful everyone shared their experiences! As someone who's been dragging my feet on selling my vacant lot for almost 6 years now, this thread gave me the push I needed to finally get organized. I wanted to share one additional resource that helped me piece together my property records: many title companies keep copies of old property tax assessments in their files from when they handled closings. I called the title company that handled my original purchase and they were able to email me copies of the assessment records from that year within a few days. Way faster than waiting for the county assessor's office to dig through their archives. Also, for anyone worried about the complexity of all this - I was definitely overthinking it. Once I gathered the basic documents (original purchase info, insurance settlement details, and property tax assessment), the calculation was pretty straightforward. The hardest part was just tracking down the paperwork. Planning to list my lot this spring now that I understand the tax implications. Thanks again to everyone who contributed their knowledge and experiences here!

If you use tax software, all of this is pretty straightforward! I moved from Texas to Minnesota mid-year and used TurboTax. The software asked when I moved and then walked me through everything. Honestly way easier than I expected.

One additional tip since you mentioned the high withholding on your extra shifts and billing payments - keep detailed records of all your work locations and income sources throughout the year. As a physician who moved mid-year, you'll want to track not just which state you earned income in, but also where you were physically working when you earned it. This is especially important for those weekend ER shifts. If you're picking up shifts in different locations or even different states, each location might have different tax implications. Some states tax based on where the work was performed, others based on your residence at the time. Also, since you mentioned patient billing payments, make sure to track any business expenses related to your work (CME, licensing fees, professional memberships, etc.). These can often be deducted, and with your income increase, every deduction becomes more valuable. Keep receipts for everything work-related from both states - some expenses might be deductible in one state but not the other. The good news is that with your income tripling, you're likely in a much better position financially to handle any unexpected tax obligations that might come up!

Has anyone considered the flipside? If the tenant pays utilities directly, does that mean the TENANT can deduct those utilities somehow? Like as a home office deduction if they work from home? Just curious if there's any benefit to the tenant for paying utilities directly vs having them included in rent.

I went through this exact same situation with my duplex rental last year. The bottom line is definitely no - you cannot deduct utilities that your tenant pays directly to the utility companies. The IRS is very clear that you can only deduct expenses that you actually paid out of pocket. However, don't let this discourage you from the tenant-pays-utilities arrangement! There are actually some advantages to this setup. You don't have to worry about tenants leaving lights on or cranking up the heat since they're paying the bill. Plus, you avoid the hassle of having to collect utility reimbursements or dealing with seasonal fluctuations in your cash flow. Just make sure you're capturing all the deductions you ARE entitled to - property management fees, repairs, maintenance, insurance, property taxes, depreciation, etc. Those can add up to significant savings even without the utility deductions.