We liked the TL home and nice lakefront view but here are some cons: pretty far/isolated, no real dining options outside and besides the music festivals/BNP tournament, didn't know if it would do well as a STR. 

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...

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.