I don't mind committing 2-5 years to get everything running and established, so long as by the end of that time frame any portfolio I have is set up in a way to set it and forget it.

One of the things I have been watching in this area are the regulations as @Mike Shemp mentioned.

Considering the ever-evolving landscape of Short-Term Rental (STR) regulations, What are the best 5 states in your opinion to build a STR portfolio starting today? 

An extension of credit primarily for a business, commercial, or agricultural purpose, as defined by 12 CFR 1026.3(a)(1) of Regulation Z.

Curious about the things i cant see on airDNA, and more about how any regulations and state/county specific costs have affected yall before i dive into a purchase there?! 

Toledo's regulations are actually much worse, with a number of investors from Toledo PIN suing the city over it.  

The wholesaler probably doesn’t believe the deal will close, just wants a contract from you and sellers failure to sell as agreed so he could establish the lost profit due to seller’s non performance and sue for the $15k differential which is easier to win rather than specific performance. 

The third zone is one that is highly regulated, perhaps taxed at a higher rate, but has an established process for STR's and the risk of changes in the laws regarding airbnb or other OTA's is relatively low, simply because those conversations have already happened and the local government has decided that they are going to allow them in the area and have an established process for permitting, etc.

The regulations are significant.

Always review your lease agreement and consult local laws to ensure compliance with all regulations.