So to close this loop for now, here are the results of my research. I'll write a quick description of each system I considered and why I used or discarded it.
The winner:
- Xero is what I am plugging forward with (thanks for the recommendation @Gita Faust .) It is like QB in that it is a real accounting software, but it seems much more intuitive, less glitchy, and a true cloud based product that feels much easier to use than some alternatives. It is easy to set up for a real estate specific business and it allows me to track multiple properties with the tagging feature, so I can drill down on how each property is performing as well as a group of tags (properties) which is nice if you want to run reports on a certain portion of your portfolio. Finally, it has a bunch of short videos that explain how to use it and set it up, and the customer support is knowledgeable and got back to me quickly every time I had a question, making it possible for a non-accountant to figure things out on their own. Check back with me in a few months to see how I'm liking it. Once I get a handle on things and have a few months under my belt, I plan on handing it off to a bookkeeper, with the bonus of understanding what is going on behind the scenes without doing the work.
The runner-up:
- Lessaccounting.com was a close second, and I played around with it for a few hours setting up my books. It is easy for us non-accountants and the support is also quick and thorough when replying to questions. They also use tags that work great to drill down on individual properties. Ultimately I chose Xero over lessaccounting because the traditional accounting styel seemed a little more standard and therefore easier for me to pass off to a bookkeeper. For someone who plans on maintaining the books themselves, this could be a good choice.
The also-rans:
- Buildium seemed like a good product, but has so many property management features that I wouldn't use. I was looking for a simple bookkeeping solution, but this could be good for someone who is more hands on with property management.
- QuickBooks is something I used for a while and I couldn't stand it. You know it's a bad sign when the "for Dummies" book is three inches thick. Also, the interface seemed outdated and stuck in the 90s.
- QuickBooks Online felt like a ported version of the desktop version, not a true cloud solution. Missed lots of features important to a real estate business, and the interface was glitchy. Reviews of it are also very poor.
- Quicken Rental Property Manager was a product that I was going to try... and then I read the reviews on Amazon. People hate this software so I didn't waste my time.
- FreshBooks had a nice properly designed interface and I gave it a try, but their rep told me it is meant for service-based businesses and mainly focuses on invoicing.
- GnuCash is a free option and perhaps good for people who enjoy spending time on their books and with the software. It is open source and thus pretty flexible, but wasn't the simple solution I was looking for.
- Wave is another free option that could be a good option for some of you out there. It is supported by ads and felt a little clunkier than Xero. I also read some feedback from people stating it could be hard to scale with, but the likely depends on your own threshold for hours/month spent on it.
- Property Solutions rep told me that they are only for MF averaging 30+ units/building.
That's it, hope this helps someone else out there because that's eight hours of my life I'll never get back. Looking forward to getting current with Xero and then removing my least favorite part from my business! If I missed any good options out there, feel free to let me know.