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.

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.

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

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

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

Account holders can't take any write-offs personally for investments made in the 401k.

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'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.

This will allow you to remove the person and do the financing on your own.Home Equity Loan/Line of Credit: Since you're looking to access equity, a home equity loan or line of credit (HELOC) can be a good option.