My idea is to offer my skills, such as social media management, painting, or assisting with various menial tasks, in exchange for the opportunity to learn the trade.

We used PropertyZar.com (full disclosure - I am associated with them)

If you associate his name with an article and its on a reputable website (news) or even just their social media, it's a quick google search for his name by a PM, landlord or interested LP to throw up red flags.

As for a Home Owner Association (HOA), whether it needs to comply depends on its legal structure and tax status.

A better approach might be to find a REI Association in the area(s) and ask other investors for their recommendations - it's not uncommon to choose a different appraiser depending on the type of property (residential vs commercial MFH vs. office or industrial) and the objective of the appraisal.

If you sell the property (regardless of whom to), you will pay all the fees and transfer taxes associated with that sale - likely thousands of dollars.  

If there’s a lawsuit or financial risk associated with the property, the LLC structure helps limit your personal exposure by acting as a liability shield.

(source Indiana Association of Realtors).  

There is funding out there from the city and other associations.

The tradeoff on the joint financing is going to be the (refi) costs associated w any transfer of ownership, HOWEVER transferring title to the LLC is unlikely to trigger due on sale (b/c it sounds like most banks simply aren't monitoring and/or enforcing due on sale in these instances) which would make the ownership (sans the actual mortgage note) more easily transferable than exiting your position as an individual owner?