I actually like them because the homeowners' association (HOA) usually covers most of the insurance, and there is very little maintenance required.

These units are perfect for owner occupants, and they are perfect for related living as you have described.

My job every month is to operate with as little $ as possible in banks that pay nothing, getting every dollar possible into my money market accts earning 4%+.

Really expedites the time it takes to reach FI when you can completely eliminate your housing payment and get into multis for such little down and start building equity/cash flow with each one.

I will have another post about it and what's going on but I have reached out to the current owners and awaiting a response they are currently wanting to sell.

@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.

2) Buy a few out of state properties over the next few years, through a well vetted turnkey provider like the one I mentioned above, which should more or less break even or give me a little bit of cash flow, and since I'd end up with a few doors my risk would be a little more spread out? 

I like A better personally as it feels a little less cramped but it's a toss up.

I brought a vision to the home that previous owners couldn't see and therefore sold.

I've made investments in Chicago, so I understand urban markets a little bit.