The rest of San Diego still has STR permits available.I am hoping for a good peak season to offset how poor the off season was.You are doing something very well if your ADR is up (or you previously was doing something terribly wrong). 

Hi Joseph, You would need a 2 year seasoning period to qualify for a government loan (FHA) and a longer period for conventional unless you had a documented hardship situation, such as medical illness, etc where the loan can underwritten manually. 

That is where I draw my take on Sell/Rent my biggest fear is the "What if Factor" - drop in tourism, association comes under litigation, hurricane (This season looks like it will be "Very" busy), Sickness or health issues or other.

During high season I will be distributing $10k+.

Depends on the market, some markets with students, and older populations do well with 1s.

Additionally, you can rent it out for a minimum of 3 months (high season in Florida), 2x per year which is very investor friendly.

@Sean Gammons rising property values & mortgage rates have ended the "easy days" where you could buy anything and rent for cashflow.You're going to have to look harder or go into riskier investments.Prior to the crash of 2008, seasoned investors would look at 100 properties, bid on 10, to hopefully get one deal accepted that met their ROI and CoC requirements.

West CV is older than east CV and is virtual certainty to  gentrify. 2) Imperial Beach (IB) is cheapest ocean properties in US for hundreds of miles.  

They seem to have some success with them but it’s pretty seasonal.

Quote from @Season Price: I am curious if anyone is wholesaling MLS/listed properties as their primary strategy?