Seems like you are going backwards to most people. If it were me, I'd spend winter on the Gulf Cost, and summer in Colorado.
As for your TT and Pickup combo, the F150 eco boost is a very good platform. However, you must be very cognizant of the payload of the F150. I'm sure the Eco-Boost has a higher payload than my 2005 F150 w/ 5.4L Triton, but you need to subtract every pound from the payload limit. That includes you, the dog, any personal stuff in the truck, a hard top cap, or hard bed cover. cover, the weight od the hitch head, plus the tongue weight of what ever trailer.
Absent accurate hard numbers, I'd use 13% of the GVWR od any trailer you are considering. Subtract this number from the payload figure also. The payload number of your truck is on on a yellow sticker on the door jam on the driver side door.
