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. 

You may decide to change your strategy a bit to buy flips worth 70,000+ which I finance myself (and others do as well) and can even refi into a 30 year once the property is rehabbed.   

However, with all due respect you have about 20 podcasts to listen to and about 2K forum posts to read first.Learn a little, ask a question, read a bunch, watch a video.Learn a little more, ask another question, read a bunch more, watch more videos.Get an idea, apply what you've learned, realize you need to learn more, ask a question about your idea, which leads to a bunch to read, and 4 videos.Modify your idea, apply what you already knew, and what the changes to your first idea taught you.

@Philip C.I don’t think tenants really changed anything unless your DTI is high

I called tenant to inform them of change of ownership and that I’d be serving them a 60 day notice to vacate.