I currently self manage my properties using Buildium and I love it especially the resident portal and ability to accept ACH rent payments.

A Class properties - you usually don't need a property manager, you just need a leasing agent and contacts to call if something needs fixed/as well as the ability to be cashflow negative for 2-5 years.

Absent that, the big differences will be which forms you report the income, your ability to deduct business expenses against the income, and applicability of self-employment taxes. 

We purchased a property, signed contract for a 45-day SoW (cosmetic rehab, add AC) and after about 30 days it's been radio silence.We have been pretty patient and now at 60-days past closing we've engaged another local PM who is going to be re-keying, assessing rehab status and taking over from here.I think similar to OP there's nothing particularly nefarious or shady going on here, but the follow-through and ability to land a deal is significantly lacking with this team.

Do you have the ability to close on the contract yourself under the terms of that contract? 

The answer is a combination of knowing the numbers, your projections of those numbers in the future, and your confidence in your ability to do the analysis. 

Additionally, a larger property like this is valued based on the actual cash flow, not sales comps, so you have the ability to force appreciation faster with efficient management.Adding the a 5-10 unit may also increase the amount of time you spend getting you closer to the 'Real Estate Professional' status for tax purposes opening up room for offsetting some W-2 income on taxes.  

I know it is alot, but I thought with a open schedule and possible ability to get this property at a discounted price it could bring in some return as I would have an easy tenant and location is perfect. 

I have some brokers telling me that it's still a rent PSF calculation, but I'm just not seeing how that's an accurate way to price it b/c of the effect a drive thru has on the ability has to drive traffic.

For me it’s really not about splitting hairs over $10-$20 a month..I just want things to run smoothly at this point.