I’d prioritize my lifestyle preference over potential appreciation when deciding between those two different environments.

Especially for E 83th St, how the overall safety in this area?

That would mean convincing everyone that a change is needed for safety issues to avoid fire hazards and to also allow for solar panels, which would be good for the environment.Sometimes HOA's forget that they are their to support the home owners and not the other way around.Do you know if the wood shake roofs are part of a historic look?

The most important thing is to build in a margin of safety, which is very hard in today's environment.

Go to the local building and safety department and bring the address & APN of the Property.

When making this decision you should factor in a whole lot of other things as well (income, retirement, safety money, etc.) so I am not going to give you advice on that without knowing your situation. 

Some things that matter:location (neighborhood, safety, freeway access, parking)amenities  (W/D, appliances, dishwasher, storage, garage, fireplace, AC, walk in closet, etc)number of bedrooms/bathrooms  (layoutcondition  (Is it clean, remodeled, dated, light and bright ...)Yard, privacy, balcony, One of the most important pieces affecting pricing is number of bedrooms.In short, spend some time checking comparables and then price accordingly.

The wife and I are seriously considering Safety Harbor because we enjoyed the area when we were stationed there in the mid 2000's.

Some like the convience of the first floor but others like the feel of safety on the second floor.

More experienced investors often prioritize items such as the value of the value add, amount of market and rent appreciation projected, how passive is the purchase, etc.It is my opinion that SFRs purchased at retail today in San Diego will have negative cash flow when financed at tradition LTV (all cash of course will cash flow).