Just out of curiosity are you trying to self manage or are you going to a property manager?

Not only is it a good idea to learn how to shoot a gun, and have your concealed carry permit, but learning self defense would help too.

You should include management (10%) even if you plan to self manage.Are there any utilities you'll have to cover?

About 50% of our Bridgeport residents live work in New York City, which is about an hour away.Housing is much more affordable for them and they don't mind the commute.Once self-driving cars are a reality and they can work or sleep during the commute, or work from home, the commute will matter even less.

Brent  I'd probably look for houses with a Realtor than self manage it if I were you.

Be confident in your rehab costs or give yourself a buffer.

If you are planning on self-managing the properties, then I suggest starting with the 1-2 properties that are the "middle" level SFH or a small multi-family (duplex / triplex).

I'm assuming you plan to self-manage, however if you consider the future you may not always want to self-manage so it's a good idea to factor in management fees when looking at properties (typically I use 10% as a management fee amount).If I use $285k purchase price with 4.990% rate and 20% down, income of $1981/month, expenses of $250/month, property taxes of $3,100/year (per your calc), insurance of $150/month, vacancy of 8%, R&M of 7%, CapX of 10% and management of 10% then I calculate you'd be a negative $593.76/month in cashflow.

Can you elaborate on how you made the transition from being the operator of the relatively "self-run" business of multi family to being the operator of a business with business hours / payroll / etc? 

Buying without even going to see the property would only be reasonable to a very experienced buyer who is confident what he is investing in and the purchase is just a small percentage of his wealth.