So you have a roof leak, the underlayment is rotted, they say they won't pay for it.

Was wondering other stuff like property management expense like getting a handyman to fix something or roof changes etc, assuming they are a bit more.

We sold a house that we had a total roof replacement, within a few year the new owner had a leak of the flashing around the chimney. 

It needed a new kitchen, new bathroom, new floors, a new porch roof, and needed to be totally rewired.   

What's the condition of major systems like plumbing, electrical, and roofing?

I would rather own 6 to 10 high quality appreciating properties than 20 to 30 lower priced rentals (e.g. replacing all those roofs, HVAC, all the tenants, turnover and property management fees).

Obviously there won't be any 100% "safe" tenants, no matter how much vetting you do, a job loss etc. could always happen to anybody... but I feel like having one at all simply shows that they didn't prioritize keeping a roof over their head for one reason or another, among other issues.Everything else from that post, if I am referencing the same one, seems fine to me.

I find it hard for the numbers to work if I only put 3.5% or 5% for down payment as the monthly payment will be through the roof.

During the beginning of the stabilization, we had a HUGE FIRE roughly $400k in damage...well after the fire our property manager did not properly secure the building and then the locals came in and stole all of the radiators, which caused leaking through the entire tier. 

I would focus on getting that househack first.You can take advantage of a lower downpayment, get a roof over your head, and an investment property all in one.