If you are considering them in this market environment, they must have some uniqueness that is worth considering.The asset and market are important but the operator and how they manage the project are critical.

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. 

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?

Swimming upstream against the rules and regulations can be difficult and time-consuming so it's best to stick with what works in your favor.

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. 

My thoughts were that I needed a structured environment and a piece of paper to let me know that I had acquired a skillset.

I worked in office environments I kind of liked it frankly..  

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