You still have to run the same process regardless as there are bum tenants in nicer areas just not as many of them.Biggest mistake I see is buyers getting sucked into the thought process of a B property running at 45% costs and then seeing a 6 cap for it and then seeing a D property at a 9 cap at an area and only accounting for 5% more costs.You have to be local to the property, expect very high management fees and a specialist company that is trained to deal with those type tenants, double bookkeeping costs for collections and payments, etc.I personally in GA have watched over the years for multifamily you could get great areas at  a 9 cap.

Good bookkeeping practice.Odds are good this contractor is asking for cash as a means of tax evasion and you would be smart to not participate.

Please note that I am strictly talking about software for book keeping purposes.I only know of Quickbooks and Sage

Do my own bookkeeping on whose money is in there, track interest for their deposits, etc.

Breaking RE materials down for 2 or 3 houses like roofing nails or sheet rock would be silly, even 20 houses a year, maybe at 200 or at 2,000 units there might be a difference.The more you try to learn on your own in finance and accounting the greater the chance that you'll mess up, you don't need to go past Accounting 101 and 102, bookkeeping and preparation of a budget, income statement and balance sheet, from there that's all you'll really need for what you'll be doing, IMO.

@Harry Williams There are methods to having a CPA or bookkeeper to separate out transactions from the same account through Quickbooks for multiple properties however, this will be additional setup and bookkeeping costs.

My only problem with that is that it starts adding bookkeeping steps.I appreciate any experience that you could provide.

I don't charge a fee on top of what they pay to smartmove-less bookkeeping for me, less income to report on, and the tenant doesn't feel like you are just keeping their money as long as you explain that the money goes to smartmove and not you. 

I currently have a bookkeeper that does all my books for my rental properties and flips.

One way when there's a deficit, the other way where there is a surplus.For bookkeeping, I use QuickBooks utilizing the class function, and I can develop a separate P&L, Balance sheet for each property, without separate LLC's.