Moved here about a year ago when the market was still favorable, but am just now getting started with investing and am in awe of the price changes I've observed...

I observed that the current trend is B&H here in HI, but that is according to realtors.

I believe that's a bit harsh; after all, mankind has yet to sample and observe any actual population of scum growing on this planet to behave so wicked as to somehow deserve such an insult.

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.