Property owners in these areas can only advertise for monthly rentals and are not permitted to offer daily or weekly rentalsandIn March (2024): Florida lawmakers passed legislation granting the state more authority over short-term vacation rentals, potentially impacting local regulations. 

Your strategy on a 5/2 is going to take a little more blocking and tackling for mid term rentals.

Given these circumstances, I believe there may be grounds for a class action lawsuit against these companies, and their owners.

There is a house (2b x 1b) in the family I was interested in becoming the owner of.

Your realtor can give you all the actual sales comps to help you see the difference between the listing price and the actual sales price.I however do have a little contrarian advice. 

@Nicholas A. your shotgun approach has a high probability of getting the exact quality you put into it.95%+ of real estate agent, many of them posting they are "investor-friendly", only know how to deal with owner-occupied transactions. 

That is fine on SFR which can be sold as rentals OR owner occupied, so you can shift your target market and still sell.

Paid a top local esigner to come have a look and all she did was insult our cute little place that was doing just fine.....But I think where a designer could add value is by suggesting unique areas, like game rooms, coffee bars, outdoor BBQ/play areas, and stuff like that. 

(Get an owner occupant loan.)Can you seller finance it for more?

For example in many jurisdictions I can STR units in a duplex but cannot STR an ADU (some jurisdictions will let you STR if you owner occupy).