Quote from @Mackaylee Beach: Welcome to BiggerPockets.

Basically AirDNA makes my thesis and I prove it against real time available data on those sites.I am not an expert in Destin but Tampa area is a similar beach market and small condo's struggle as you are competing with hotels to an extent. 

Tax reasons, lower cost of living, wife is Brazilian and has friends already living in Orlando area, beaches and most cities are within a few hours drive. 

I sell real estate to STR investors in a beach market, and one of the main strategies I tell them about (and that I also use myself) is to have a new 4-point inspection and a new wind mitigation report done periodically and to reshop insurance with a few BROKERS.In Florida, these inspections are only good for 1 and 5 years, respectively, so you MUST get new ones--especially if you have had a new roof, added hurricane clips to an existing roof, or replaced your wiring, HVAC, water heater, etc.Also in FL, insurance companies come and go, so there is no need to stick with the same one and just take it when they try to bend you over and raise your rates. 

I have invested a total of $285K in... a beach front lot 2016 and beach front condo 2017; both in Brazil.

I have never tested it in court but reviewing the lease it makes it clear that unless otherwise agree the rent is automatically increased at lease end to the weekly rate as its a beach property.

As others have said, you need to look at the whole picture.Somebody buying an oceanfront property in Laguna Beach might be happy with a 2% cash-on-cash return, because they are banking on appreciation.Then somebody buying a 12 unit apartment complex in Cleveland might not do the deal unless they are getting a 15% cash-on-cash return because they are going to see very little appreciation and will need to deal with headache after headache.If just evaluating the cash flow, a cash-on-cash return of 10%+ is right to me.

STRs usually do better when they are at destination locations such as beaches, lake homes, mountain cabins.... 

I am literally sitting on the beach right now and I have guys doing three renovations, two rental returns, and walking two properties.

If you are still at $300k you will not be in the pretty section which is close to the beach.