It seems like the condo you linked is almost geared towards short term rentals, so you should be in the clear on this specific situation. 2) I would take a look at some STR data either via a dynamic pricing software (pricelabs, wheelhouse, etc.) or take a look at Airdna to take a look to see what is the “sweet spot” is in terms of size of rentals in your market.

Pretty sweet arrangement! 

In my free time, I'm a wine/food guy who loves to travel. 

I'm not so sure and I think some are finding out that it's not so easy.Agreed, Lane basically sweet-talked me into this thing saying it was the 'safest play' out there and an easy 10% and I fell for his b.s.   

I think it might be a sweet spot for my price range.  

Conde Nast Traveler recently announced their 'Top 10 Trips everyone in the US should add to their bucket list' and it features some impressive vacation regions and activities:- Hot Air Ballooning, New Mexico- Bluegrass Trail, Virginia- Visiting Point Dume Malibu, California- Horseback Riding, Wyoming- Airboat tour Everglades, Florida- Winter expedition cruise, Alaska- Spiral Jetty, Utah- Camping In Acadia National Park, Maine/Rhode Island/Massachusetts - Trekking the Bayou, Louisiana - Wine country, Willamette Valley & Napa Valley Oregon/California 

Don’t want to start renting to some wine if I’m not doing it correctly.thank you

Since you are focusing on 30+ days walk into the lobby of an extended stay hotel (Homewood Sweets, Extended Stay America, Choice Hotels with Extended stay etc.) and look for the reader boards.

I think that is the sweet spot. 

Short and sweet, shoot me a message if you are an investing agent from Louisville.