This reply does not apply to the financing issue but rather, combining all rental properties into one LLC. 

Its a great combination to create some margin in your personal finances without paying tax.

Unfortunately, the duplex utilities are combined as one (the duplex shares the ac unit, water, and electricity). (1.)

You've most likely visited Cleveland already so use the "Ultimate Guide" as a BASIC framework, combined with what you saw on your visit and determine where you want to buy.As an FYI I do know of a lender that will do mortgages for properties in the $40K to $50K range in Cleveland so if you need their info, let me know.

Someone comes a few days later, was here for less than an hour and left.  

To determine the treatment of section 1231 gains and losses, combine all your section 1231 gains and losses for the year.If you have a net section 1231 loss, it is ordinary loss.If you have a net section 1231 gain, it is ordinary income up to the amount of your nonrecaptured section 1231 losses from previous years.

No other credit card, student or car debt.Will a mortgage broker look at the finances and say no, you can’t afford both your personal rental and an investment property since combined they become over 43% of income?

The current rent at $1200 is lower that what rentometer estimates in the area, which is $2k combined for both units

If neither of you have money and are saving a combined $200/mo, you’re looking at almost 20 years until you can afford a down payment on a $100k property (not accounting for closing costs, reserves, etc).

The property has 3 floors with in unit washer/dryer, ample storage, intercom, central A/C and 2 deeded parking spots and is also within a 5 minute walk to the Roslindale Commuter Rail station.