Until you have enough properties to justify the expense of an experienced bookkeeper do it yourself.

It would be difficult to justify a 10 year life expectancy for the $2 blinds you get from Walmart.

I'd also love to hire someone to handle the complicated parts of this situation if I can justify the expense.

Regarding your specific questions, I don't think you'll get enough of a benefit from a higher floor to justify the additional cost.  

This means high-profit margin on the flip (+40k or +22% ROI) but less than desirable LTV which is crucial for a refinance and your eventual cashflow.The issue with going for a Grays Ferry, Brewertytown, True Port Richmond, East/Olde Kensington, Point Breeze is that your debt service will be so high due to the cost to compete.I'll shoot you straight with this strategy, these places you will not see full gut rehabs now nor will you see a baker's dozen of comps to justify full cash-out refinance.

If you have to turn your units over every year, or if your property does not attract responsible tenants, it might be hard to justify the hassle of managing them yourself.Managing the properties is pretty easy when you are not turning them over to new tenants.

This thread had downplayed the importance of understanding cap rates for the OP, but cap rates are huge part of this business and for us larger multi-family guys, an extremely important metric in negotiation and causing a seller to justify their price.

You're trying to justify the purchase price as an investor.

They can determine a higher value though...so you have to be confindent that your evidence justifies a lower value.There are professional companies out there that will fight for you. 

However, even if it was not the tenant's fault, the tenant's lack of reporting the issue still shows a level of incompetence/negligence that puts you at serious risk--and which more than justifies looking into eviction options (or, at minimum, not renewing their lease).And, as others have mentioned, there are a litany of other serious red flags here from the tenant and the PM that justify corrective action on your part.