We keep seeing conflicting views but my personal experience with buyers indicates that the outlook is positive.   

Costs ran significantly over on both of these items and not being in the area it was not possible for me to add my experience in renovations to lowering them. 

Wait a couple of years and use your investment knowledge/experience along with your equity to invest in other properties i.e. those located in less expensive markets.All the best!

@Jared LeggettFrom my experience, house hacking in NYC is doable, but it often means looking into more affordable neighborhoods or smaller properties.

Anyone in the community who is already operating STR in the Westchester county area who can share their experience with starting a STR specifically if any particular permit is needed to operate such a business out of an owner occupied residential unit?

Looking for good first hand experience with a recommendation... just what every landlord wants, someone who knows what they're doing and is reliable.

Thank you for the kind words, it's been an interesting experience so far. 

@Nathan BrooksIn my experience, connecting with like-minded investors in Richmond can be done by joining local groups like the Richmond Real Estate Investors Group (REIG) and checking out BiggerPockets Local Forums.

Not impossible but the more issues the project has, the more experience a lender will want to see.

Everyone has different experiences.