I've been toying with the idea of buying a winter getaway home, one I could rent out Airbnb/VRBO April-November.

This particular deal is a little different from your normal investment as it's intent is to be rented until my family and I are ready to fill it's walls with our own photos and it's floors with my sons never ending accumulation of toys.

The only thing that I’ve been toying with updating is the kitchen; that’s something I may do this month.

My only limiting factor currently is the finances to toy with it all, but I am trying to educate myself in advance, so when I'm ready later this year, I'll have the knowledge by the time the money is here. 

I have been toying with the idea of buying one and adding it as an optional item to rent.

Are you the type that buys the fancy watch & car today or do you invest such that the investment funds your toys in the future? 

Also maximize your options by NOT spending on things that depreciate like cars and electronic toys.

When things get worse and the government is unable or unwilling to keep pumping out cash.Like the fabled grasshopper, you are dancing in the fields enjoying the sunshine and we wise ants are toiling away... because winter is coming.

I think having this at a lake with lake toys would be successful.I'd create a nice outdoor area with firepit also.Try searching on VRBO and see if you can find some similar to this.

Sewer and drain back up example would be your tenant's kid shoving a toy down the toilet.