Our philosophy, vetted investment opportunities, means we focus our efforts in locations and segments that have historically provided stability, and are currently undergoing above average economic and demographic growth.

I don't love the area, but it has about a 95% historical occupancy.

A lot of investors typically avoid these because of the initial costs and length of time it takes to do the work, but I enjoy the challenge and would much rather do a major renovation on a historic home than multiple cosmetic remodels for the same amount of initial capital and return on investment.

I understand we've kept them at a lower rate to ensure their stay because historically they've been great.

HOAs are not always receptive to providing financial data or historic data regarding assessments (could be an indicator of poor maintenance budgeting) so you may want to use your realtor as a source to pursue getting details about the leak and the financials.

I use far lower than San Diego historical property and rent appreciation numbers. 

Area code 77701( Oaks Historic District )  specifically. 

I guess on a basic level but historically interest rates have little effect on housing demand and I don’t see if dipping much as rates rises.

@Lucien PerreaultNo offense to @Jeff Bridges but I would not invest in RE if I was only expecting an 18% return and historically in San Diego for financed buy and hold the return has been significantly greater than 18%. 

Shepherd is a historical town with lots of old buildings and such that have been restored and they get a lot of tourism because of it.