This is not specific legal advice, just my opinion based on estate planning/asset protection background.  

Rental income/collections are strong at 100%, but cash flow can be choppy with capex/maintenance along with timing of expenses like when all my prop taxes are due.

Any pointers on who to avoid would also be helpful ;) Obviously this is one of the pieces that can make or break the performance of a deal, so I’m trying to cover all my bases as much as possible

You are pre-approved based on your status and employment so if nothing changes, you are good to go.

Unicorn deal (they exist - we found one this year)I'd strongly advise staying away from new MFHs in this area - the supply is now exceeding demand. 

Chicago has also seen strong appreciation in both home prices and rents the past few years.Worst part - Don't get lured into the D class neighborhoods because the cash flow looks good on paper.

Being cloud based has the perk of tons of freedom and less time constraints for meetings and trainings (but with the advantage of them being there every day if you want them!).

Northern hills and neighboring fort mckinley are really coming on strong in the last few years so you could get some very strong price appreciation.

You're generally seeing $150-$200/door unless you do a really strong BRRRR and pull out most/all of your capital (then it tends to be less). 

Based on your goals, experience level, and my assumption that high earning w-2s tend to be demanding of your time, I actually think that there are better ways for you to offset your w-2 income.