Enclosed a few pics for your reference.Should I involve the HOA?

If your new servicer wants to play games, file a complaint with the CFPB and dispute with the credit bureaus.

So this involves hiring an architect draw up plans ($1,000 - 3,000 if I had to guess).  

When doing a full due diligence on these companies, I found out that their trustpilot rating was 1 star and read several lawsuits filed against them, by multiple homeowners.

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

Many real estate agents dabble in property management without fully understanding the complexities involved, making it risky to work with them.

The FBI’s Financial Crimes Unit investigates these matters for filing of charges on Equity Skimming violations.

I work on projects across multiple states and have a strong network of contractors.Regarding when to involve a contractor, if it’s someone you haven’t worked with before, I’d suggest waiting until after the inspection.

But make sure you make a file labeled "why I intended to hold this and what changed".

It depends what basis you are filing under.