The cool thing is you have multiple strategys and just because you choose one, does not mean you cannot switch to another one - maybe one fits your short term goals and another one helps down the line with long term goals.

Further, I’ve had rental property since 2010 and a short term rental since 2016 - not sure where you get your stats from.

I indeed have learned a ton from them in a very short time. 

Short 1.5 minute video walk through of all of the rooms, bathrooms, common areas, etc. 

@Jack SeidenGreat question: I am 60/40 stocks and real estate right now, excluding my primary (my investment in BiggerPockets as a private business). 

I've done Crypto, stocks, businesses, ecommerce, trading bots, ponzi schemes etc. 

The idea is to find a pocket or neighborhood that offers the right combination of estimated ROI and rental demand, giving a balance of cash flow and tenant demand.In my view, this approach provides a more reliable signal of demand than relying solely on pricing adjustments or short-term market trends.

If in the rare chance they do allow short term rentals in the HOA rules/regulations and association documents, don't be surprised if they change that ruling after you buy. 

It’s a long game so worrying about the short term is kind of pointless.

I'm interested in trying the short-term rental market with a couple waterfront properties.