I'm going through the same decision with our lake house. One thing nobody's mentioned yet is the 14-day rule. If you rent it for 14 days or less during the year, the rental income is completely tax-free and you don't even have to report it! You'd still get all the second home deductions too. This might be a better option depending on how you plan to use the property. We only rent ours out during a local festival when rates are super high, making about $9k in just two weeks, and we don't have to pay taxes on any of it.

Quick advice from someone who's owned several vacation rentals: Be super careful about community/HOA restrictions! Many gated communities have strict rules about rentals, including minimum stay requirements (often 30 days) or rental caps. Make sure you check your CC&Rs before making any decisions. Nothing worse than buying a property planning to rent it out and then discovering the HOA forbids short-term rentals.

Make sure you file your taxes ASAP! My ex's girlfriend tried claiming my kid a few years back, and because she filed before me, her return got accepted first. I had to paper file with documentation proving my case, and it took MONTHS to get resolved. The IRS basically treats it as first-come, first-served until someone contests it. If you have documentation showing your kid lived with you for more than half the year (school records showing your address, medical records, childcare receipts, etc.), keep all of that handy. Also, check your divorce decree - sometimes there's specific language about who can claim the child in which years that can help your case.

Make sure that if you do agree to let her boyfriend claim the child (which it sounds like you shouldn't), you DO NOT also claim the same child on your return. If two people claim the same dependent, it triggers automatic flags in the IRS system. When my brother and his ex both claimed their son one year (miscommunication), they both got audited, both returns were held up for 8+ months, and they had to provide extensive documentation. Both ended up getting hit with penalties even though it was unintentional. Also remember that if the boyfriend improperly claims your child and gets caught, he could be banned from claiming certain tax credits for up to 10 years. Might be worth mentioning that when you explain why he can't claim your kid.

Try looking for a tax professional who's building their client base. I found my accountant when she was just starting her independent practice after leaving a big firm. She charged me $525 for both my personal and small business returns (home bakery). She was building her portfolio and wanted the experience with different types of small businesses. Three years later she still only charges me $625 even though her rates for new clients are much higher now.

I guess I'm in the minority here, but I actually think $1,100-1,500 isn't outrageous for combined business and personal returns depending on your situation. I paid $1,200 last year and felt it was worth every penny because my accountant found nearly $4,000 in deductions I would have missed on my own. She also helped me set up a better bookkeeping system that's saving me hours each month. Good accountants do more than just fill out forms - they provide tax planning, help with estimated payments, and can advise on business decisions throughout the year. If you're just looking for someone to input numbers once a year, then yeah, go cheaper. But if you want actual tax strategy and support, sometimes paying more is worth it.

Just my two cents - I've been a tax preparer for 6 years, and here's how I feel when friends ask me for tax advice: if it's a quick question that I can answer in a few minutes, I'm happy to help. If it's something that requires me looking up information or running calculations, I usually say "That's something I'd need to research, so I'd have to charge my regular rate." Most tax pros have a professional liability if they give incorrect advice, even casually. So sometimes what seems like us being stingy is actually us being careful about giving advice without proper documentation and review.

My mom always brings cookies to her accountant during tax season just to be nice, not as payment, and he often throws in some free advice when she picks up her completed taxes. I think building a relationship is key! Maybe start by asking just 1-2 specific questions and see how receptive they are? If they seem happy to help, great. If they seem hesitant, back off and offer to schedule a paid consultation.

Just a quick bit of advice based on my experience as someone who's filed with 1098-Ts for years: make sure you understand the difference between Box 1 and Box 2 on the form! Box 1 shows payments RECEIVED by the school, while Box 2 (on older forms) showed amounts BILLED. The IRS cares about what was actually paid (Box 1), not what was billed. Also, don't forget that you need to subtract any tax-free educational assistance (scholarships and grants) from the total qualified expenses before calculating your credit.

Has anyone used TurboTax for this situation? I'm trying to enter my son's 1098-T but it keeps asking who paid the expenses, and I'm not sure what to put since the money came from several different sources (my account, his savings, and his aunt).