With lack of experience back then (only had a few single family/duplex units under my belt), I invested passively in a couple of deals (an 80-unit and a 164-unit) with the goal of starting to understand the business plans and to interact and work with people in the space that were taking action.

An additional element to consider are the property taxes in Indiana.

The 2nd level of criteria you have is more realistic but again, I think just having ONE of those elements will be pretty good. 

It was middle of the summer, it rains a lot in the south and people need their roofs doing what they are suppose to do, (keeping the elements out.)

I've also recently started interacting here on the forums at BP.

Understand Where the Risk LiesOf course, there is always going to be an element of risk when you screen and approve a tenant you’ve never met before.

It is far less simplistic, but also beneficial because we have the opportunity to build passive income over time just by interacting with other agents. 

Learn how each element works but hire it out as you grow...contractors, property managers, attorney, accounting, etc. 

So while you may be working on a wholesale deal today, that doesn't mean that interaction won't lead to another real estate transaction later. 

I typically try to repair them appliances can be expensive and I do appliance repair myself so to someone it may be a huge deal but to me new heating element or new stove eye repair will save you money in the long run especially around property tax time