For instance, FHA guidelines are very strict and restrictive when it comes to using departing-residence rental income to qualify for a new FHA loan (such as the 100-mile rule).

While I don't believe that you need a full blown business plan, strict operational budget, timeline, scrum board, etc...

As you may be aware, the City of Asheville (about 2/3 of Asheville is in city limits; the rest is under county jurisdiction) has had strict STR regulations in place since 2016.

Yes, because Private Money infers that you are in a negotiable deal where your project can be outside the box and you can negotiate unique terms with a private individual - that - or a big box lender with strict rules and guidelines. 

Co-ops have strict subletting rules that can change anytime, which could make things tricky.

Also there is strict no refund policy, even from your wallet.

Would you avoid investing in strictly a cash-flow market?

I'm not sure which places are best to focus on with rules and regulations getting strict in some places. 

I've been saying this for years.Norada Capital is not strictly a syndication, but rather was selling high yield non-collateralized promissory notes, guaranteed only by their private company for which they give no financial description of what the company does or how it makes money on their website (Marco does describe the business some in an article below).

Someone who knew how to juggle those strict timelines and anticipate the tenant-related curveballs.