I would trust them to do this as they have already been handling all the small maintenance themselves and organizing professional repairs when necessary, which we deduct from rent.

In order to organize your search, create a spreadsheet and gather the following data points for the past 5 years for at least 7 midwest markets:- unemployment- job growth- job diversification- income growth- population growth- home pricing- rent affordability- vacancy ratesAlso note, landlord / tenant laws and property tax ratesOnce you have this, order your search based on trends (there isn't a perfect market either). 

Further, we don't know how the OP is organized for federal income tax purposes.Thus, the conclusion that the lender has a 1098 obligation is premature. 

Right off the bat I could tell that he is super organized and thorough which was imperative for me doing an out of town flip. 

His is a quality organization, that I recommend you look into.

If my Austin friends have some good REI meetups that they might recommend for a young person just starting out, looking for house-hack, then by all means, please chime in.This thread is as much about talking to grown up kids about money (or anything else) as it is about house-hacking, so looking forward to useful and insightful responses.

Contact a few lenders and see what they say.If you try 5, you will likely get 5 varying answers.It will also help you organize your info and numbers.

What programs/software do you guys use to organize your network of investors/cash buyers?

In most cases, leads that show motivation have a problem "right now", and showing up in Google search results via organic or paid allows you to try to provide them with a "right now" solution. 

The guest speakers that come through are always commenting on how large of a group we are and how well run the organization is, so I guess that's a good thing.