Hawaii STR or San Diego LTR?

[Mika Manzo]

Hello from a new member!  I am trying to make a decision and was hoping to pick some brains from people with experience. 

We currently live in San Diego and have a LTR that’s doing fairly easy, profiting about $300-400 after paying the mortgage.

My family and I are ex-kamaaina and visit Oahu often. So I got this crazy idea, what if we sell the LTR and use the profit to buy a condo in Waikiki? So we have a place to use, and rent it out when it's not in use. (I'm sure I'm one of the many who has the same thought.) I've been researching regarding STR in Waikiki, tax, etc. If we are to buy, it'll be the legal condotel.

But after crunching some numbers and noticing high HOA+fees, in today's tourist economy after COVID, I'm not sure if it would profit enough to surpass the current LTR, especially when the LTR in San Diego market also has the potential for future value appreciation. I don't mind at least breaking even for the first year or so, but wouldn't want to jump in if there's not much profit even when the economy bounces back. I'm also wondering if the condotels are overpriced, now that many illegal ones are getting shut down. But when the tourism is back, wouldn't these condotels go up in price even more?

Is it worth it? 
Any opinion, advise, crystal ball prophecy appreciated!