Henry Washington from BP on the market podcast operates here.

While I have none in this market I have been on one realtors monthly newsletter with market analysis for over 8 years. 

But for the best local advice, make local connections in the market with Host groups and Rental Associations.

I suspect maybe something like Hagerstown or Cumberland, which yeah are Class D like markets with declining populations, high drug problems, no strong job base which leads to non paying tenants.

A portion of rent goes to the purchase price which is on the top end of market value. 

I guess with certain markets its achievable!

My main job is running my investment holding company, so I'm familiar with public and private market investments but new to RE. 

It's a free market. - You will finally get a tenant. 

Quote from @Marc Zak: In the market where I live (San Diego), appreciation has been strong and many predict it will continue to appreciate in the long term.However, with current interest rates (6% at best) and property tax (2%), the annual cost burden is 8%.Am I correct in saying that appreciation has to be above 8% annually (plus whatever my maintenance and vacancy costs are) for me to make any money in this scenario if the property is cash flow neutral?

Until the lease ends and then the legal notice time in your market has passed.