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.

If something happens in the future in regards to STR regulations, you would be poised to restart your AirBnb business. 

Due to the pessimistic outlook with regulation around AirBnB's I think house hacking via AirBnB is only a good idea if you can ALSO make it work with a long term rental in case things go south. 

My family and I have used the strategy with bungalows where we bought older properties that were in need of lots of renos.The reno costs were between 30-60k and we put non-regulation suites in both houses.

I'm not getting much feedback from the government office in charge.