I'm considering purchasing a condo or a small SFH in the Oceanside/Carlsbad area as an investment property and renting it out on a short term rental site like AirBNB. 

Medium term rentals may be a better option.

(These are 2 of the shows I listen to, so you’re capturing much of the market.)Thanks for all the effort either way. 

FOCUS ON SELLERS, NOT BUYERSWe have a term in the real estate industry "Listers Last" Simply put this means that real estate agents should focus the majority of their attention marketing to sellers, not buyers.

Shorter term CD's actually have higher rates than longer term so staying in the 3-6 month range is best.  

It is in the area that has decent short-term rental rates based on airdna and what property managers are seeing.How much more in maintenance have you all noticed on a short-term rental versus a long-term rental?

Finding an engineer that's highly regarded locally can help slipstream your efforts.

By BRRRRing, you can achieve your goal of acquiring four houses with minimal effort and financial strain, allowing you to shift from buying to paying them off.

I would try and manage it yourself if you have the time and effort. 

@Kavya VeerapaneniThere is a market for short term rentals in Danbury.