@Lorelei HilzSurvey's (improvement) are not usually recorded so you won't find them online and it won't be in the appraisal district records in the rare event a survey is recorded.  

Madison Street has a pretty decent shopping/restaurant district.  

However, this house is in a historic district and I had a few questions:1) Being that it is in a historic district, who do I need to contact in regards to finding out restrictions on what I can / can't do to the house?

Using comparable sold properties with similar condition to your end product, within a 1/2 mile (sometimes a little further), less than 6 months old, within 20% of square footage, not crossing major boundaries ( high ways, school districts, city lines, etc).

Right now my wife really likes Kenwood, Coquina Key, and Grand Central district but i'm not sure if those are great investment areas. 

I currently work in I.T. at a school district, and I am definitely looking forward to leaving the I.T. world. 

Only family friendly park in the best school district in the area. 12 cap in California. 45 spaces.

I always track areas with good school district because people are always trying to get their kids into those areas.

Are there activities in town such as parks, museums, theaters, colleges, highly rated school districts, etc.

Also, you can command a higher rent for the same unit sizes in the City (excluding the Center City District).