@Jared Stone..another Jared responding =)  The main issue I see with your property with many DSCR lenders is the considered 'small' loan amount

Tenant mentioned he would rather deal with me directly as he just messages me if he has any questions.

We have a mixed bag of federally subsidized, as well as non-federally subsidized rent assistance programs, many which abide by rent assistance Housing Quality Standards requirements.For Housing Quality Standards, screens are not actually required...if they are present, though, they must be in good condition so as to not posed a cutting hazard or other health and safety riskHope that helpsHi Connor, is there a website you could direct me to that tells me requirement/criteria for rent assistance for both landlords and tenants in Milwaukee?

We would encourage them to share the good, bad, and ugly so you can gauge whether we are a good fit for your investment needs.While it's true that many of our clients haven't directly come from this platform, I'm excited to be part of the BiggerPockets community now as well.

The small multi-family and MTR approach can be a good one.

Would love to connect with you as I am originally from the area and can point you in the right direction with refis/buy and holds. 

The reasons are 1- less competition in commercial2- greater property types lead to more opportunities for “value added”3- commercial net income projections include expense for property management, 1-4 unit residential usually do not4- greater “universe” of properties to buy allow higher minimum return standards Of course residential is MUCH easier to successfully deal in, and with reasonable leverage has small downside risk, so I 100% agree that most investors should stick with residential.  

I know the due on sale clause is unlikely to be called by the bank, but don't want to sell with even a small mortgage balance left.Seller finance is to lessen the cap gain/depr recap tax hit.

The project life cycle to the end will cost at least 22k or more, even on small deals of purchases prices under 100k. 

@Roseann Koefoed,As long as you have legitimate self-employment or an active business, you will be able to establish a self-directed Solo 401k plan.