Driving through Matlacha to get to Pine Island was particularly tough to see. 

I’ve done two rehabs from out of state so far, and I can relate to the challenges you mentioned.One thing I learned the hard way is that managing rehabs remotely can be tough.

Landlording is an exciting (and sometimes tough) journey to embark on. 

So, while it’s possible, it’s tough to find deals that fit these strict criteria.

Closed at End of Sep2024 and listed on Zillow and other sites via Turbo Tenant.Compared the comps via Rentometer ,also offered 1000$ off for first month rent .I hear winter is a tough time , should I take down the rental listings from Zillow and other sites and relist when it's Spring?

You can present an offer that aligns with your financial goals, but be prepared to walk away if the seller won’t negotiate to a price that ensures you’re not left in a tough financial situation.

Looking for suggestions on any specific building materials, fixtures, accessories, furniture, and tech for a STR.  

I can analyze LTRs more easily due to the availability of the material information.

I do have a third goal, but too much will happen by the time my second goal materializes that my third goal will likely change drastically.Also, I tend to find myself wanting to ask market-specific questions to agents/lenders/investors/contractors/etc. a lot.

Maybe go to one in a tough neighborhood so you really get in the thick of things.