You just have to create your own opportunities and markets, and niche.I agree with the Gentleman above stating the STX has less tourism traffic then Thomas or John.

One family friend who has been a season investor from Hawaii told us that we should try to get the plan and permit now and wait for the next down cycle to build because of the high building cost.

I know new construction must be to code, but what about older buildings? 

I was talking with another gentleman, Bob, who owns a lot of property in the area.

Is it the seasoning, cost, or what is the reason for that?

I  would search for rental property located  west of highway 87 and  be very careful of older, often non conforming property in downtown San Jose. 

Some houses are seasonal (April thru October) and others are full time/winterized.  

The house is in what I'd classify as a B neighborhood consisting of good schools and nicer older homes.

Are there any seasoned wholesale investors willing to school me to the game?

Some amount of base pay, and then 30 different types of bonus, missed lunch, overtime, etc, pay.Until you've been doing it for two tax seasons, we will only be able to use your base pay and rent from the other three units to qualify you.