I had to really look into profit and loss accounts and understand how the numbers worked.

Tenants often appreciate transparency and may be more understanding of future rent increases if they are aware of the property's maintenance challenges.Consider a Sale or 1031 Exchange: While you've expressed concerns about commission costs, it might be worth re-evaluating the long-term benefits versus the immediate costs.

I understand it is a difficult market at the moment (High interest, High prices, etc), and I have no problem playing the waiting game.

You and your friends should not be messing with this when you don't understand these concepts well, and they are confusing.- rentals do not go under an S-corp, which is why a separate PM company was suggested- S-corp technique on reducing SE tax is both tricky and costly, and you cannot set up your salary arbitrarily- you can only base your 401k on the part that IS subject to SE tax- you usually cannot generate enough "earned income" from this 2-companies setup to make it worthwhile for 401kSee, it is not simple.

From what I understand some people are just wired different and can totally function off less sleep per night.

However, you need to understand the process and what products are available to you, so meet with several and ask lots of questions. 

I understand the varied success and experiences with section 8 rentals but the lesser home prices in the area are intriguing.

We understand we need a lawyer to create a warranty deed but we have some confusion on how to handle to tax portion.

Also, a savvy tenant who understands what is needed to rent and what you need to provide to them before collection of rent could call L&I and report you if you have not done everything by the letter. 

Milwaukee has been very competitive, anything decent sells with multiple offers, the houses are old and OOS investors often don't understand how delapitated the place is they just bought.