If your vacation home happens to be located near a major event — like a PGA golf tournament or a big multi-day concert — you may be able to rent the place out for a short period even at high rates and pay zero federal income tax.Tax-smart year-end strategy: The more rental days between now and year-end, the better — as long as they don’t exceed 14 days for the year.Rented more than 14 days with substantial personal useYour vacation home falls into this category if you rent it for more than 14 days during the year and your personal use exceeds the greater of:(1) 14 days or (2) 10% of the rental days.

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.

I think a biggerpockets poker tournament might be fun especially with all you high rollers lol.

If it comes from memberships vs. events/tournaments that is important.

Yes if he can play steadily over the tournament any big soccer club wants him after:).

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....

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.

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...

Patty's day of course, rugby tournaments, and occasional trips to Wet Willies).Welcome to BP and RE!