The way you are structuring this deal, you are likely creating a security, which means that the transaction is now regulated by the SEC and their rules. 

Because housing is higher priced and rates have risen, your underwriting should be more conservative.  1) Use 10% Cap Ex, 10% Vacancy, 10% Management and see if it still cashflows. 2) Check HOA's fees and dues, as well as HOA regulation. 

It has been addressed by local government as a crucial need in the area as well.

We will see how this plays out, but I am not real optimistic.Lesson, STRs can be regulated away. 

Am I missing anything in terms of regulations or general market dynamics that would cause these prices to be lower than other, comparable metro areas?

While this is a good thing in some ways, as it keeps the power to change taxes local to your own community, it does mean that the state government can’t act to regulate or influence this taxation.

It may also be that local banks would rather not deal with the onerous regulations of an FHA loan and instead are steering you towards other products. 

The government gives me a break of over half a buck on every mile I drive to my investment properties and back, landlording.

Also, is there state laws or regulations to do wholesale transactions.

The property is zoned R-6 and in the Citizens Guide to Residential Zoning Districts & Regulations on the Richmond City website R-6 properties allow for "One dwelling unit located in an accessory building, containing two or more stories (lawfully existing prior to the date of this section), with conditions" ... which to your point sounds like accessory units are only "grandfathered in" .. still I will reach out to the planning department for more information.