Willing to pay a premium! 

HSA money is instantly available (all of it) for qualified medical expenses (medical office visits for doctor, dentist, optical, mental health; prescriptions for most meds, procedures, even Medicare premiums when he gets there).  

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provide support for the property tax appeals process.

This arrangement would cause use to miss out on the long term vacation planners but also there might be a premium we could charge by being a short notice STR, much like airline charge more for tickets closer to the day of travel. 

I would also decide if there is a premium to be paid to live in this HOA? 

If it becomes unprofitable to operate then converting to LTR is an option or just selling altogether, there is no initial purchase price premium for it being a STR.

The ROI on your own advertising won’t justify the cost unless you have a TRULY unique property, but even then it should get booked solid at premium rates in the big platforms. 

Those “premiums” to build during Covid are evaporating just as fast as they went up.

Virtually nobody should knowingly want to allow someone like yourself to arbitrage their property unless their is a huge premium or profit share. 

I've got a full time job elsewhere, and want a modern, reliable building that attracts reliable tenants in a good area while thinking about this from an investor's POV.Goal 1: Build and live in a premium unit for myself.