It’s a little more work to set up, but if you get a solid property manager, it’s not as scary as it sounds.If I were you, I’d keep digging into the Capitol region, NJ, and CT—compare the numbers, and maybe even start building connections with agents or wholesalers in those areas.

@Stacey OlsonRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

It’s time to look into home owners/rental insurance.

John I rented a 4 plex i remodled in charleston as the flip market had slowed.. the tax's on it were substantially higher than an owner occ property.. could be the rates were different this was a 1.2 mil prop..

That Chicago near Southwest side is a great little area. 

Hey Jeff without knowing any details everything is what you are able negotiate. but you have to take in account the years interest rate and purchase price and what kind of cash flow.I will say get a mentor if you’re inexperienced these kind of deals can go left if you really have little knowledge when it comes to structure .

We're still waiting for the owners bank to let us know if they'll actually help us or not.

We should form a little group and share info as we have similar backgrounds.

The current owner bought it for $30K and I know they had to clean up a lot of title work and started doing repairs. 

Upside is that you are paying off debt a lot faster with more towards principal and less towards interest. 20% down is only for SF, even a duplex will require 25% down unless owner-occupied.