When a vacationer has a choice of ski lodge condo (right next to the slopes), casino hotel, motel, or house, they often choose the former before the latter.  

For example, my wife who does STR PM has systems in place to help each new renter find the property, she then helps them understand specifics that are new to vacationers (the mountains and the winter are not what everyone is use to), she has a system in place to get them new towels if they run out, and responding to a broken water heater is important but different in STR vs LTR. 

OOB or more Oceanside Biddeford provides another option- rent to students then rent weekly to vacationers during the summer and students like that so they do not have to pay for a full year.Good luck! 

Ww currently rent to short term (3 to 6 months) however since we are not on the beach we don’t attract the vacationers.

Baldwin Lake, Fawnskin).Those are some thoughts and some tips to stay close to capitalize on the weekend, or summer vacationer. 

(we like the idea of condos by the beaches we live by for vacationers).

That will give you a clue about what matters to prospective vacationers.

Hey Chad,If a vacationer is injured (God forbid) you can potentially be in a heap of legal trouble if the basement isn't up to code/living standards.

Wife and I are looking into REI down in SD for vacation rental near balboa park-- Hillcrest or North Park area vs other....1) Does anyone have any particular recommendations for a real estate realtor that is experienced in transactions for someone like myself... ideally looking for duplex/multifamily that can support at least a few vacationer parties at once... would be likely using Pillow or other "turnkey" to assist since we live in NorCal to rent out VRBO/AirBnb/etc. even if lucky a short term renter for 3mos on local contract work.

The economy is driven by vacationers so rules outlawing STR is not very likely.