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.

Appears the PMC has done a terrible job of communicating expectations with you about their services.Regarding the tenant that wants to pay 12 months of rent upfront:1) They better have great credit or no-go.2) Have them prove they are an engineer with a copy of their degree.3) Get last year's W-2 to prove they were working. --- How will you know W-2 is not fake?

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.

We're a couple big manly men so we go upstairs and there's a couple bedrooms and a small bathroom, but it is crazy cold up here, like ten degrees colder than it is outside at least.

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

Hey @Ignatius Okeke - you're facing the same wall that most newbies face when they enter: everything works to a certain degree. 

It obviously turned out to be the wrong time for an investment of such a degree.

When I allowed HH properties at my company, we screened people to the degree we could (credit, background, income, rental history), but you still end up with some percentage of "crazies" who can derail the entire property and force out your other tenants.  

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.