We are looking to buy multifamily properties and get away from long term single family rental houses.

All year round North Conway and Jackson host monthly activities like Apple picking, Pumpkin carving, Host all the Major Holidays, Christmas, Thanksgiving, Easter, Mothers Day, Fathers Day, Halloween, Turkey Trots, Winter Ice plunges and more. 

My $10k example was admittedly unrealistic.However, by way of further background, @Dustin Heiner wrote an excellent article on this topic on his website masterpassiveincome.com titled "What to Do When A Buyer Backs Out From An Assignment Of Contract".In it he suggests a scenario where the assignee decides not to proceed, perhaps after discovering a big ticket repair item that would cost significantly more than the portion of the assignment fee held in escrow. 

It is a huge ticket item and can eat ~30-40% of my reno budget.Today I did a walk through with plumbers and contractors.

As I mentioned in my original post on here, the warmer summer months will take care of themselves, but if you want to have the STR operating all year round, the winter months require much more effort to make your property a place people will want to visit and stay even when the weather gets nasty.Nothing against VRBO, but I would also take a few minutes to check out what listings are available on Airbnb as well. 

We put in a trouble ticket and had it done in a week or so.

So far, I'm leaning towards an underground pool since it can be used all year round, but if I find a property that has room for both, then I may try to incorporate both amenities since families and the older crowd are my preferred avatar.

That's how they get away with it. 

In South West Florida, there is the SWFL REIA which in my opinion is a really good group with people that give you access to a lot of valuable information and people you can partner up with.There's also the Collier and Lee County Round table which is a lot more informal and also smaller than the one mentioned above.

If you own the property in cash, you can get away with whatever insurance you want and can even get $700/yr for a duplex.