My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

Brick v.s siding and covered v.s no converted parking also make a large difference and are items that have to be adjusted for. 

"In addition, a fee of $40 is added per month for shared utility of water, sewer, and trash."

And it is absolutely true that as you try to add new areas of focus quickly you are adding more variables and moving parts making the problem harder to solve!

Large companies, like those on the S&P 500, last on average for 18 years.

It’s great to hear you’ve found a co-host you like, but I’d also suggest adding an investor-friendly real estate agent to your team.

Left some of the character while adding modern amenities, brought it up to code, and staged it.

I have a duplex that I originally intended to have serviced by individual heatings systems, but ended up installing a single system that's large enough to heat the whole building.

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You could look at “FIG” (fourplex investment group) I get ads from them occasionally.