If you want to originate and sell jumbo loans, there is an investor market that buys those loans, aggregates them, then pools them into securitized bonds. 

That's the same logic that'll be applied for anything from a unicorn statue you mount on the roof to an ADU to an extra bathroom, for some of those things the data will exist (full ADU, and an extra full bathroom, view of one of the iconic Bay Area bridges), for others it will not (unicorn statues, unheated outdoor swimming pools in Alaska, sheds, view of one of the iconic Bay Area bridges also winds up here sometimes too). 

Pools are harder work than expected, Flooring is my thing, Allow more time for projects than expected (especially if you have a day job), You can do 99% of the work yourself if you have to.

Sunny

Expected rent: $1500-1800Expenses:Mortgage/Tax/Insurance: $520.20 HOA: $300 (Includes trash, structural insurance, pool, and tennis court)PM: 10%: $150Cap Ex: I'm unsure on this.

This should open up the buyer pool to a more competitive set.

I also in the past have always personally met with accounts I've used since they were local; is it worth branching out to have a broader pool of candidates?

Riley military base so the tenant pool is deep!

I find myself looking for houses in good school district only and find it hard to get a good deal obviously.2) What do guys think of houses with swimming pool ?

My kids now have a pool and we just got a trampoline so I can do my work 100% in my home.