I spent about six months researching the area and the options, making about 40 offers (some of which ended up going for 100k over list), and looking for a "deal;" the prices went high enough that I nearly threw in the towel, but my numbers, discussion with current owners, and observation of traffic and occupancy over that time seemed to still point to a robust STR market.

I searched 3 bedrooms in a very tight area and it went from 65 to 33 when I filtered by 'Instant confirmation' Very good observation! 

My observation is that SFM owner/manager in our area tend to keep the 1st term so that lease ends in Summer (June-August).

Is the cash flow, or lack of, worth the realistic likelihood that San Diego property is going to continue to appreciate at the levels observed over the last decades?  

I concur with Kyle in many of his statements of observation, as I have seen the same in the greater Burlington area.

All that said,  I'm speaking from observation and questions I've asked to authorities,  I've yet to have a voucher applicant even apply after I discussed qualification standards with them;   and nowadays my PM handles it all.You might want to go straight to the horses mouth and ask https://www.kcha.org/ on this, since getting it wrong may open you to a discrimination (on source of income) claim.   

Of course there are cycles but it's nearly impossible to predict or observe them prior to their taking place.

Careful about discouraging others here, based on your feelings and observations.

But to share another perspective, I've seen anything 'of significant value' that does actually go to auction in WA - especially with a structure- of any type- go for (honestly) quite close to the mls/fair market price, and some- (when the full range of issues/challenges & unknowns about structure/condition were taken into account)- likely went for more via county auction..This is just my personal observation bookmarking, watching auctions, and doing significant title/etc research with the intent to bid/buy in some cases- across western WA (Specifically the last 3-5 years).

@Hector Espinosa: You are an observant fellow.