Towing a 27 foot trailer is same as towing a 10 foot trailer just corner little bit wider nothing to it you'll do fine, yea you'll want a decent trailer brake controller and trailer mirrors / mirror extensions so you can see around it. You'll want to be able to see what's next to you on both sides clearly you won't see much behind it but not a problem.
long trailers are easier to back up too!
Take little time read the the instructions fine tuning the controllers setting, you want them to work with each other truck and trailer when slowing or stopping from low as well as high speed situations. Enough braking force applied for those oh crap moments people will surely put you in time to time but yea light enough so doesn't skid or do all the work at light brake pedal type stops. Choosing settling in on initial gain setting takes a little trail and error until happy with it.
I put the swaybar on ours but with very little tension set almost none at all. Depends on where the axles are located the trailers weight distribution over them and where the weight is placed inside the trailer. Goes to tension setting on weight transfer springs too, how much is needed a well balanced load won't require much keep headlights down on the roadway where they belong, hitch weight is a good thing but too much is just that, too much.
Heavier items / supplies stowed forward and kept nearer the floor, lighter items toward the rear and up high same time keep total hitch weight in mind. Might need to go over that with your wife a little bit, if for example she handles that aspect such as mine always has the loading of food and supplies.
1987 F250 RC 5.8L C6 4x4 4.10LS (Parts)
1994 F250 RC 5.8L E4OD 4x4 3.55
1995 F250 SC 7.5L E4OD 4x4 3.55
1997 F350 RC 5.8L ZF 4x4 3.55