If you have never pulled......go slow and learn. As a general rule, if you are uncomfortable - leave, slow down, or stop.
Watch the whole LOLOHO series of videos and any others that pop up. Watch the Colonial videos on your trailer model. Read all the manuals. Spend as long as you can with the trailer deliver walk through.
Your trailer hitch may not be correctly setup when you pick up the trailer. Read the tow vehicle and hitch threads that apply to your rig. Don't be scared, just informed.
Towing a trailer is not like driving a car. You need to actively drive the rig. You need to practice defensive driving and look for what might happen before it does.
The traffic cones are a great idea. I use them for a guide and also to show the spotter where I want to go. Some folks do not have a spotter. It is good practice to use one. However, you are responsible for where you drive and back. A spotter should not be the primary control on your backing, just a backup system. We saw a fellow at JC back about 3 ft and get out and check. Then he would back a few, 2-3 ft, more. That is not a bad plan. He learned to to it the hard way. There was a big bash in the rear of the trailer that he was at JC to have fixed. Don't let that happen to you. It can happen to all. We talked to a lady who is married to a truck driver. They had an older trailer that is narrow. They purchased a new 25 and guess what. It didn't fit beside the house the same. Eves tear up trailers. Look up as said before.
Look down too. Those tire treads that big trucks throw from time to time are a real hazard. Try not to follow trucks too close. You can't see the tread they just hit if you are too close. You can't see the chuck hole they just hit either. Ten miles an hour slower will lose you 80 miles a day. Might have to drive for another two hours or take an extra day to get there. Damage to the rig costs you a lot more in the end.
If the 27 has ST tires, they are likely limited to 65 mph. You may only drive 60 mph, but if you pass someone, you can get the speed up a bit in a hurry. You do move on when you pass, right. Also, if you travel long distances, that extra 10 mph kind of pulls at you. Driving over 65 builds up heat and shortens the life of an ST tire. Read the Marathon and Michelin threads. Don't be scared, be informed.
Wind has a different effect depending on the TV hitch and AS that you configure. Force projection works different from brake pad friction, cam or spring bar sway control. Worth reading those threads as well.
Sway and wind buffet are two different events. Learn the difference and what to do. In a sway condition, apply your trailer brakes. In a wind buffeting condition, do not over control. Slow down in 5 mph increments until you are comfortable with the result or stop for the night and get an early start in the morning. Wind often builds in the mid day period. We get caught trying to make some miles after it calms daown in the evening. Makes finding a good camping site a bit difficult when you get there after dark.
Daily distance is another challenge to consider. We watched a few videos of folks who traveled 200 miles and stopped for the night. In our car travel days, we often traveled 600-800 miles. That difference kind of concerned us. Consequently, we did a trial trip and found that we could easily make 400 miles in a reasonable day of travel. We calmed down a bit. Think of it as slow and steady does the trick. After all you are pulling your shell behind you.
Take a few shake down trips. A 2 hour drive, not too far away from the dealer is a good start. Then go for a days drive to a destination you like. Soon, it's vacation or road trip time.
Transition major cities in the non-commute hours. We would not have gotten through ST Louis without both of us paying close attention to directions, signs, and traffic. The trip North to South through Salt Lake was horrible around noon because of the truck traffic. The trip East to West after 6:00pm was no trouble at all. You have to take it the way it comes and stay calm. Try to travel early in the day to arrive at your campsite in daylight. Help other drivers when possible by slowing or moving over. Do not feel you must be in the curb lane. Often it is easier for entering cars to avoid you if you are one lane over. Somehow they just never see you and never step on it to get out of the way. Plan ahead, watch how the truckers drive. You can learn a lot, but beware of the one that keeps weaving. He may need a rest stop.
If the trailer drops off the pavement, do not jerk it back in to the lane. Trailer and TVs end up out of control and roll over when that happens. Slow down and wait for a place to safely pull back onto the pavement. Folks with more experience may have better advice on this one. You have to watch the transition on highway pullouts just like service stations. ASs like smooth pavement or very slow speeds.
Go down hills at a reduced rate of speed and maintain that speed with your brakes and at least one gear lower to provide some engine braking. Apply the brakes for a period of a few seconds and then back off them to allow cooling. Remember your trailer brakes are drums. If you brake to about 5 mph less than your target speed, you can release the brakes and let the rig gain speed until it is going faster than the target speed before you can apply the brakes again. Your trailer brakes may need adjustment to help with smooth transitions. Worth discussing when you pick up the rig from the dealer and read the threads. Makes for a lot of evening's entertainment.
My brother purchased a 1/5 ton, hooked it to a SOB, and used a clone brand hitch. He drives about 60, sometimes a bit slower when there is a head wind. He made it all the way to Maine from Montana and enjoyed the trip. You can too, just take it slow and drive the rig carefully.
Travel safe with your new AS. You will enjoy the smiles from the miles. Pat