I would like to buy a future retirement home to get away from the cold winters but in the meantime would love to rent it out as a vacation rental.What are the good areas to consider and where would I get the most vacation renters and cash flow?

This way you can utilize the leverage if you plan to scale up in the future.

Hi Ursula,Even though this post is a few months old, I thought I’d chime in just in case you’re still working through this or for future projects.

This led me to have an extreme ambition of trying to give my future family the things I didn't get.

Disallowed losses under wash sale rules increase the cost basis of replacement securities, potentially reducing future taxable gains.This post does not create a CPA-Client relationship.

Luckily you will be in a class and larger group of investors and future investors looking for a good deal to participate in. 

This could help protect against any future lawsuits. 

It does however give you a degree of independence to choose what you want to do.As your portfolio grows you'll also feel the weight of future capex responsibility more, which ironically points you to growing more cash flow through more real estate.The other issue is that you are chasing a moving goalpost.

I would say go for it if that is what you expect to incur in the future or you are still growing.

(You know you’re on the right track and you insure future leases end between March and July by varying the length of the new lease.)Good luck.