Additionally to the other comments, the decision to use management software relates to the cost of one's time; in other words, what opportunity cost is your time / money?  

And you need to weigh those pros and cons to make sure Section 8 investing is the right decision for you personally.

These transactions don't included additional expenses the business incurs like meals, travel, dues, subscriptions, marketing, accounting, licenses, phone, internet, etc.

They also are making all the decisions on the property. 

It isn't something you will be using on a day to day basis to make decisions and take actions.

Generally most private money lenders are going to play a lot more conservative but be able to close faster/make a faster decision on lower risk deals. 

Some have a major decision right to force a sale, some would extend, others may convert to common equity.

(We're aware of the five year look back period for Medicaid eligibilty but it's not a big factor in our decision to do this.)We would get the house appraised so we can document paying FMV.House would be purchased with cash (it's a small home in a rural area and value is low)Inlaws would sign a lease so that it becomes a legitimate rental and we can deduct expenses, etc.

It sounds like you're doing a good job of educating yourself which is great, but you can educate yourself as much as you want, however without a direction or destination in mind you'll never have enough information to make a decision. 

This analysis will actually help you determine how much cash you need for your first deal which will guide your decision for a well paying facilities job.