Usually the property is bigger and can command a good nightly rate.

I connected with David Fritch: https://www.biggerpockets.com/users/3cityDave. 

I specifically need really user friendly accounting features (including ability to sync with quickbooks and print checks directly from the site/software), customizable online application, and online rent-pay as an option (hopefully with free or very cheap ACH). 

Check out FilePlace, where user-created forms are available for free.

Buildium our property management software does not provide credit bureau reporting as service, despite request over many month from many of it's users. 

Real Estate Rewind Starting over http://www.biggerpockets.com/files/user/brandonatbp/file/real-estate-rewind-a-biggerpockets-community-book Good luckPaul

So a question you should ask yourself is if your condos have strong appreciation potential/future owner user, or are they more limited and seen as only rentals in the future?

Contract marked owner occupied, there is NO tenant in subject or proof tenant moves out, no rent back from seller... you cannot use rents to qualify, do not rent the property, there are ways this is checked and considered dishonorable.Your wife and children can move in and you can come and go as your service requires. 

This means that it doesn't possess a user-interface that would allow you to make modifications according to your needs.

But if you are committed to purchase, a 2/2 would prevail over a 2/1, the price difference has to be nominal and now you might attract a different user like tow couples or adult friends that don't want to share a bathroom vs a young family that the kids are okay to use the same bathroom as the parents.