And while it might not be attractive to all real estate investors, I believe it can be a fantastic way to start to build experience, build profit/cash flow and establish yourself as a STR professional in your market and then use that to build a co-hosting/management business and work with investors that want to you use their knowledge and expertise to partner on projects.Point is, don't believe everything everyone says about what is "bad" and what is "good".

Obviously, the Margaritaville Brand is very strong and they have great amenities, but is it universally appealing so you attract as wide a demographic audience.

Too many folks think that physicians have deep pockets (if we do, it's not from just being an MD), so we are an attractive target for lawsuits.

When considering properties, focus on accessibility to popular attractions and amenities, as these features tend to attract more renters.

Make sure you consider not only what attractions are near by but also the saturation (or lack thereof) of short-term rentals.

It also shows sellers that you are a serious buyer, making your offer more attractive in a competitive market.

Is there anything you mentioned/listed specifically that would attract an insurance company? 

Doing so places all involved parties at risk, and I fear will attract the attention of legislators thanks to those who do things carelessly.Instead, stay in the deal by closing on the purchase and selling with a wrap.

The wife and I considered doing a game room but were afraid it'd attract the wrong niche.

They are cheap because they are undesirable and will attract crappy tenants.