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 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 would still focus heavy on stocks/index funds.

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

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

Once it's rented, use that rental income to help offset your DTI, which may help you qualify for the second property sooner.Partner with Investors: Team up with someone to split costs and lower your personal DTI impact.

Personally, I started my investment journey with multifamily properties before moving into single-family homes.

Not a lot of our competitors offer this but it's something we can consider (but for us, it can't be in a rural area, the loan amount must exceed $150k, if we're using PadSplit income (or STR/MTR income) the max LTV is 75% and the down payment must come from your own funds). 

I'm assuming you're referring to investors that provide all of the funds for your flips? 

The challenge was balancing the relationship between landlord/tenant and a personal/friendly relationship.