The good news is that I've won a lot of money in my poker "career" (mostly in higher-stakes cash games, not tournaments).

For my husband, travel to every major golf tournament for a year....

I made a killing on weekend tournaments(~500-700 per weekend) You can pick up night games and men's league softball games that are after 5:30PM.

There is a major golf tournament hosted in Orlando every year (Arnold Palmer Invitational).

I grew up in New England (Massachusetts) and used to do a lot hockey tournaments and hiking in NH. 

The PGA announced over the weekend that the 2022 PGA Championship, one of the tour’s four major tournaments, will no longer be played at Trump’s golf course in Bedminster, New Jersey.

That is a great bio with some amazing accomplishments (looks like you did great in DI and even made it to NCAA tournament and did well on the national level in Greco, too)...No doubt you will have the drive and will power in any area...

About 3 years ago I played a 100 dollar poker tournament that won me a seat into a 365 dollar tournament.

Festivals, college graduation, fishing tournaments etc.I adjust my price through out the year based on demand, events, and time of year.I have accounts at Homeaway (also searchable on VRBO) and AirBnB.Homeaway and VRBO blows away the bookings I get on AirBnB for vacation rentals so I would use the data from here primarily.You can also check local Craigslist ads  for properties similar to yours to see what their pricing is.Also look at their requirements for security deposits, pet fees and cleaning fees to she what you should be charging for these also.Once I started getting reviews on Homeaway my calendar started staying full.I charged on the low end to get more reservations in the begging and once I had several 5 star reviews then I started charging on the high side.

Also, Flamingo is building a new 191 slip marina, just completed a major fishing tournament for offshore fishing.