After crunching the numbers it seems planning on a 10% vacancy rate and factoring in a property manager the cap rate should still be close to 20% on the buildings I'm looking at. 

Its in the Old Colorado City (some compare it to the next Denver or Portland with the "hipster"/millennial influx) with unobstructed views of the mountain range and Pikes Peak, which really drive up cost here. 

@Bill Brandt my brother just bought a three-bedroom two-bath in Fort Walton Beach it's right beside Destin and just a five-minute Drive that's starting to be the next option to be close to Destin

Not an excuse, but the reality the kind of chaos, confusion, and exploitation that happens after a hurricane.So, when I end up getting someone who's available, with a chainsaw, able to take action, who's offering to help clear the debris off the roof, who's driving a truck "BLT Trees and Landscaping" but said it will be all cash, I yielded. 

Costs associated with them and trust factors?

I agree, investing here in my backyard is ideal, especially for my first few times because I want to be able to get intimate with the end-to-end process and ideally be close enough to drive to my properties within a short time.

Say 15 minutes driving, maybe 30 by transit, which I'm willing to do. 

I laugh every time I drive by it.

You should absolutely make sure all costs are factored into the NOI.

I have been logging some serious driving for dollars time and i have a list of approx 43 properties that i have mailed to in the past month.