You can request those tenants to clean the bathrooms through rotations or just charge them a small cleaning fee to hire cleaning crews to clean the house 1-2x a month or you do the cleaning yourself to save up money and have extra passive income.

I want to build a rental income portfolio in milwaukee.

Heloc I think we could get $175k, maybe DSCR, I am a veteran with service connection disability rating 40% but with my mortgage and car loan not sure I could make debt to income work.  

Also, will I continue to get the W-2 Tax benefits using the STR loophole if I move these properties into an LLC?

To some capital, as long as the product is not traditional vertical, apartment-style product then it is still build for rent.The biggest evolution I have seen in Build for rent recently is the transition to multi-parcel and for sale/for rent hybrid developments which is contrary to what was more standard in build for rent 5 years ago---traditional single parcel developments for density and tax purposes.

My W2 income is >$550k/year, if I build an RV/Boat storage facility, will my storage business expenses/losses be able to reduce my W2 taxable income? 

If your LLC earns a profit on fees it earns from property management you will owe self-employment tax.

Your “rent” is going to be the landlord’s principle, plus taxes, plus insurance, plus their mortgage interest, plus profit.

I've always thought Chicago had outrageous property taxes.

This does not include any tax prep.