An alternate and cheaper plan for the door would be to change it to glass or add a glass side panel too.

I would then shop around for different hauling companies to get the cheapest price you can and i would check into if you need dumpsters or not, you may have to pay your own hauler but may still be able to put it in garbage cans. one thing you should look into though, if you now have to pay separate for garbage removal, make sure you get either reduced taxes or some kind of credit back every year from the town for the change. i know the town that i live in does that with commercial properties.

Return to date should have anything thing to do with it since you can't change the past.

Hacking your first property and then maybe a second one a year later will change the financial trajectory of your entire life, even if you don't do anything further after that.Welcome to BP and to Milwaukee! 

That will dramatically change what financing abilities you have at your disposal. 

I’m not sure how versed you are in doing taxes so Do your taxes yourself and give them to a few CPAs  to review and if nothing is better or if changes are made you will have a clear answer and it shouldn’t be that expensive. 

I feel like I have my bases covered, but am wondering if I'm missing anything obvious or if you have any tried and true questions that help weed out the bad ones.Overall - can you help me get over the fear I'm having about handing my units to a company who (seemingly) will sweep in, re-lease to their paperwork (thus charging me 8 re-leasing fees), disrupt the tenant and their current habits (all of which are well-trained save for an older Section8 gentleman) and ask them to make changes? 

The TCJA made unfavorable changes for hobby related expenses.A lot of moving parts here that you're asking about.

We basically just notified the companies that the trustee on the accounts was changing from my father-in-law to my wife (the successor trustee) and she took over control of the accounts. 

Once the ownership of the home changes, the IRS liens can be removed with relative ease, as long as the owner receives nothing from the transaction.