It will take forever for this stuff to dry when it's freezing in the house. 

I do not see this "fireside sale" lasting forever.

Ideally buy, fix, rent, refi the cash back out, and keep as a rental forever?

One clue is to look at pricing of similar houses on Homeaway and see if they have some elevated rates for events.

The is a rule which most states follow that says that any agreement for longer than one year (statute of frauds) must be put in writing to be enforceable so it cannot go on forever, but even 10 months could work a huge hardship on you. 

Want to keep the property forever - - - armor all the doors, windows and external fixtures and it starts to look like Ft Knox or the Alamo.

You could learn forever.

Great job - owning a bunch of houses free and clear myself, I know how nice it feels to have something that's "yours" (OK, despite the fact that you only really rent the property forever from the city/county/municipality, as you pay mandatory property taxes).

Justin, you may want to read Buy and Hold Forever, it is a great book for understanding the advantages of purchasing better properties.We started int he low end properties, and they are cash flowing and starting to appreciate a tiny bit.  

If buy and hold, I know this is a forever-going debate, but I'd suggest Baltimore County rather than the City... there are more rules and hoops to evict a nonpaying tenant in the City.Also!!