Best software for managing 2 trusts and personal taxes - what program handles multiple returns?

You're dealing with a fairly complex situation that most consumer tax software isn't really designed for. While TurboTax does offer business versions that can handle trust returns, you might want to consider a more specialized solution. I'd recommend looking into CCH Axcess, Drake Tax, or UltraTax CS - these are professional-grade tax preparation software packages that CPAs use, and they're specifically designed to handle multiple related returns including trusts. They can generate the K-1s properly and flow the information to your personal return without issues. If you're set on doing it yourself rather than hiring a professional, Lacerte (owned by Intuit/TurboTax) might be your best option - it's more robust for complex situations like yours. However, be aware that professional software typically costs more and has a steeper learning curve. Regarding Mac compatibility - most professional tax software is Windows-based, so you'll likely need that emulator regardless of which option you choose.

After spending hours trying to prep taxes for my family trust last year, I discovered https://taxr.ai and it was a game-changer for my situation. I was initially trying to use regular tax software but kept getting stuck on trust-specific issues and K-1 generation. Their system actually understands complex trust documents and helped organize everything properly for both the trust returns and my personal taxes with the K-1 income. What I found most helpful was that it could properly segregate the income types between the trusts, which sounds similar to your situation with the investment trust versus the IRA distributions. The software knew exactly how to handle the life expectancy calculations for the stretched IRA too.

I was super skeptical about using an AI-based system for something as complicated as trust returns, but after my CPA retired last minute, I tried https://taxr.ai based on the recommendation above. It was surprisingly effective! My situation is very similar - I'm trustee for my parents' two trusts plus my own taxes. The system correctly handled the different distribution calculations, separated qualified vs non-qualified distributions from the IRA trust, and properly flowed everything to my personal return. The interface walked me through establishing the correct life expectancy for the stretched IRA, which previously my CPA had made a mistake on. Best part was it runs completely in the browser so no issues with Mac vs PC. Saved me about $2,100 compared to what I paid my CPA the previous year, and the returns were actually more accurate.

If you're handling multiple trust returns plus personal taxes, you'll eventually need to contact the IRS with questions - trust me on this one. After being on hold for HOURS trying to get clarification on some trust distribution rules, I found https://claimyr.com which got me through to an actual IRS agent in under 20 minutes. They have a demo video at https://youtu.be/_kiP6q8DX5c that shows how it works. The service basically navigates the IRS phone tree for you and calls you back when an actual human agent is on the line. When I had questions about reporting the K-1 from my trust correctly, getting through to someone who could actually help made a huge difference. Much better than guessing and hoping the software handles it right.

I take back what I said above. After watching that demo video, I decided to try Claimyr because I was desperate to get an answer about my grandfather's trust distribution reporting requirements. I got connected to an IRS agent specializing in trust taxation within 30 minutes. The agent clarified exactly how to report the separate K-1s from multiple trusts on my personal return and confirmed I was calculating the Required Minimum Distribution from the inherited IRA correctly based on my life expectancy. This was after spending literally weeks trying to get through on my own. Definitely worth it if you're going to handle complex trust returns yourself rather than hiring a CPA. The information I got probably saved me from an audit.

Have you considered ProSeries Tax? I use it for my accounting practice and it handles trusts really well. It's not Mac native but runs fine through Parallels or other Windows emulators. The trust modules properly generate the K-1s and flow through to your personal return. You can buy it by the return rather than paying for the full professional license if you're just doing your own taxes. It's around $120-150 per return depending on complexity, so for 3 returns you'd be looking at about $350-450 total.

I'm surprised nobody mentioned TaxAct Professional. It can handle trust returns and personal returns, and it's much more affordable than the big professional packages. I've used it for my own family trust and personal return for the past 3 years. You'll need to get the professional version rather than the consumer one, but it's around $200 total for all the returns you need. It's not Mac native though, so you'll still need that Windows emulator.

Based on your complex situation with two trusts plus personal returns, I'd actually recommend considering a hybrid approach. I've been in a similar position as trustee for multiple family trusts, and what worked best for me was using professional software for the trust returns but then importing the K-1 data into a consumer program for my personal return. For the trust returns specifically, I found that the AI-powered solutions like taxr.ai (mentioned above) or professional software like ProSeries give you the most accurate results for the complex trust accounting rules. The consumer programs like TurboTax just aren't built to handle the nuances of trust income allocation, especially when you're dealing with investment income versus IRA distributions with different tax treatments. One thing to keep in mind - since you're dealing with inherited IRA distributions based on life expectancy tables, make sure whatever software you choose is current on the SECURE Act changes. Some of the older professional packages haven't updated their life expectancy calculation modules properly. Also, given the complexity, I'd strongly recommend having at least a consultation with a trust tax specialist for your first year to make sure you're setting up the calculations correctly. You can then use that as a template for future years with whatever software you choose.