I've done similar things in a more enterprisey property management space, and the amount of data that you're managing on a single property (or 2 or 3 properties) with a single user doesn't look like enough to really justify $234/yr, and all of the things that you've listed involve trying to sort out a product issue with a marketing/business solution (which works, but only to an extent), so you can A/B test all you like, but if people don't think your product is worth it, they're never going to get started or pay for it.
From a pricing perspective, I'd rethink the bottom level plan, the pricing timeframe, and if possible the price-point (maybe shift to something that scales more with use, eg resources or features, rather than something inelastic like # of properties). Be more upfront about pricing - the "try it free" should have the pricing list - you're selling a financial product to people who are presumably good with money, but hiding what it'll cost in the features page. Having a "forever free" plan that's severely limited (/ad-supported) will help with your initial conversion.
For conversion to paid subscriptions, you need to convince them that you're better than a folder on their HDD, excel for financials and their contact list/calendar on their phone. At the very least you need to look at interop between MYOB/Quicken/CSV/whatever's the rage these days. You can focus on how computers crash so a doc library is better, or you can add a feature (versioning, archival of email, I don't know) and use that to sell the document library. If you're targeting the guy who's got 1 property, maybe get some boilerplate forms or checklists and put them up there somewhere. If you're targeting the guys who have 10+ properties, focus on exposing what reports can do. Definitely do allow users to, at the very least, download excel / other spreadsheet versions of their transactions (and if you do this, specify that you do it on the features page).