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

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

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.

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. 

With cash value life insurance whatever is left after paying salesperson's commissions is earning a nominal return, you don't have the ability to invest these funds (unless you take a loan from the policy, think of this, you have to borrow your own money and pay interest to the insurance company on the loan!

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.

I have a visa and although there are advantages to having my visa for lending and travel, it also allows me the ability to live in the US without restrictions that a Canadian would have without one.