The true value of RE is in what those two items represent in the form of future cash flow and property value. 

This property will require minor updates to capture top dollar for rental, but the property is in great condition overall and is well worth the effort.This is a property that I am personally investing in and that I work diligently in finding for any of my investor clients.

It has not caused an issue because I value the learning I had to do to complete the above mentioned items.

Do I have to fill out a separate Federal 4562 for each item and check it off as bonus depreciation, or can I bulk the items together - either all of them total, or the 15s together and the 5s together?

I'm offered seller financed package by a wholesaler. Only info presented is that all properties are rented.I plan to ask for rent rolls, what else do I need to know (watch-out-for's) in this pursuit?

Real estate investor, if you did a cost segregation, amortization, depreciation, 1 time expenses, 1 time closing cost Fee's and this can differ from residential financing compared to 5+ financing.  1 time expenses on properties can be new roof, appliances, A/C and bigger ticket items. 

I have a list of items my PM is recommending to meet the section 8 standards, I want to make sure all of them are necessary.

No bread and butter items purchased only business costs to make money.  

See notes on Rehab Cost Estimates for why this is too low... should be at least 5% + amortizing the cost of any major capital items coming up in the next 5 years. 

@David Traeger I know the Milwaukee market well and have a couple of quick hitting items I can pass along to give you and overview.