However, I pay an additional $100/wk for their guy to go and maintain the property, plus I pay for contractors to maintain the pool, landscaping, and other maintenance and repairs.This is my first property so its definitely posssible that I could be getting completely ripped off.

The place looks pretty solid outside of a 70's tile kitchen counter and somewhat sparse landscaping.

You should account for landscaping and snow removal since it is a multi.

Option 2: Rent $1500 Taxes - 325 Insurance - 73 Maintenance -75 Management - 150 (even if you do yourself, you should budget for this) Vacancy - 120 Cap Ex - 75 Misc (Admin fees, landscaping, tax prep, etc.) - 75 Expenses $820 (I did not include utilities because normally tenants pay for that, but find out what is common in your area.Net Operating Income NOI (Income - Expenses) = $680Cash Flow: $680 - $1134 debt service = -454 You will not cash flow on this property, even if you get $1600 for rent and self manage, so this option is a no go.

that $50 dollar bill you gave to the landscaper?

I will be in Pensacola middle of next week around 19 Feb looking at the local landscape.

They take care of all the outside, including landscaping and exterior painting.

They also use a network of in house vendors from landscaping, to painters, to insurance agents and lawyers. 

(granite, new fixtures, new cabinet doors, new wood/carpet, new paint, new toilets, landscaping, seal/spray the tub, new lighting, new doors, etc).

My HOA is great never complaints about minor things like paint color or changing landscaping ect.