If you bid more that the property is worth in it's as is condition, then you don't have enough collateral to protect your investment. 

Buildium does offer the ability to interface with Quickbooks through API and offers custom buildouts.

Sure, but I agree that until you really know your problems with scale you can't justify the cost of a custom or premium software solution.

If the two are afraid for their well-being most places have laws in place to protect them by letting them out of leases-given it is usually women escaping domestic violence.

We are in a business/ venture that requires more customers, not less to charge more.

I’m of the opinion that when my contractor gets there biweekly to mow the lawn is fast enough to change them but we do pride ourselves on good customer relations.

They have no authority in the county run areas and if the county changed their rules they would run afoul of state protections.

I've taken all the major options to consideration such as book keeping, accounting, taxes, payments, maintenance/trouble calls, price of software etc.At this point, I'm looking for the most balanced option that will best help protect myself and my assets.

That leads me to believe they would want to protect their reputation.

In Orlando, you need $15,000 worth of arcade games and some cool custom lighting to be middle of the pack.