I want to exit as I don't get any personal use from the STR being 20 mins from home and would rather apply the capital to another opportunity in multifamily (LTR) or another STR in Hawaii where my brother is a broker and now manages STRs.

We are now at 21 doors under management and 3 are personal units that we self manage.

Yea this is a long-term personal play more than a strict STR deal. 

This is advantageous bc later you have a third party loan (not your personal money) so seasoning period is 90 days to DSCR out. 

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

I also personally feel like I may take a step back from my main biz in about 15yrs..

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.

I've sold over 80 homes personally in the last 30 months and I'm usually within $5k of the appraisal report when I run my CMA for clients.

@Malcolm Brown Are you planning to purchase a property in your personal name or via an LLC?

I personally think being a landlord in Chicago is easy and I have never had an eviction.