With trailer prices, I'll keep rolling into the track with the ugliest, Section 8, 22 year old , full of hail damage trailer.

I'm not in the market for one, so I haven't kept track of what they're selling for. WOW...it's crazy what trailers sell for now! It was 10 years ago, but we paid less for my basic 24' Haulmark WITH a matching numbers plum crazy '71 Demon 340 sitting in it than what just the trailer sells for now!
I've had a lot of offers for my truck lately, but it took me too long to find one exactly like I wanted when I bought it. No way I could replace it now. Plus I do NOT want anything newer.

Never been a fan of enclosed trailers Long, heavy, costly, etc, etc.
I have always been happy with open trailers. Sounds wierd, but i like people seeing my car going down the road.
I recently had a custom open trailer built to my spec. Its 23 feet long with a tilt deck. The tilt deck allows me to load the car, and literally sit on the trailer to attach straps. No getting on the floor to do so. I have a hard time with that.
It also has a fixed platform( separate from the tilt deck) on the front to load my golf cart, with slide out ramps. I paid 5200 bucks for this whole deal, buddy owns a trailer sales business, they make open and enclosed trailers across town from the retail lot.
I would wager i could get close to twice what i paid for this trailer if i sold it. 2600 pounds, tows super nice

I've had both but, we do a lot of night racing here and after , we just hang around so , I sleep in trailer .. too old to sleep in pickup .. I just sold my nice open I had built , tried that again for 3 years

I hear ya…85-90% of my racing is done at my home track 30 minutes away. I park by friends that sleep at the track, and i drive home if its an extended 2,3 day event. Come back in the morning.
Couple Mopar events out of state i go to, same thing, but i get a hotel room. It all works out well.
And the loading an unloading this trailer at my age is a breeze..probably the most important factor.

While the open trailer is nice for nostalgia reasons, the enclosed far out weighs those. My enclosed trailer is my garage on wheels. Get home late at night? No worries. No need to unload anything. Just lock it up. Full weekend at the track? Plenty of space in front of the car to throw down a cot, and sleep. I like having my stuff locked up, and secured. Rain delay? Car is inside, and not getting wet.

While I do kinda miss "showing off" the car going down the highway on an open trailer, I love my enclosed. I take so much crap w/ me to the track (tools, fuel, nitrous bottles, etc.) that an open trailer became a pain. Throwing everything in the back of the truck...then worry about rain, etc.

I have two enclosed trailers and an open. I think we all miss the days of the "rolling car show" with open trailers. But at some point for many they become impractical to race out of. Especially for those of us that race out of town at multi day events and carry spare everything with us as well as tools golf carts shade coolers etc etc. The other impractical part is having really low cars. All of the cars I have only one will go on the open trailer without issue and thats the 64. Hard to get low tube chassis stuff on all but the most pricey opens and forget about a 250" dragster on one. I dont sleep in my trailer but have seen some really well equipped for doing so. But I have a diesel pusher for those times anyway.

A new 2022 RAM 1500 Express is around $80K, Laramie is up around $110-120. A 2500 Laramie is around $160K

Because of supply issues, a 2021 model is priced higher than a new one. Crazy times

Wants and needs have always been consistent. Auto manufacturers have over 100 years of empirical data, on how to make consumers justify the unjustifiable.

I dont take a lot of stuff. What i do take goes in the truck. If it breaks, it gets fixed back home so don't bring lots of parts. As far as rain, yep been caught in that before, but its very seldom. I don't race when its gonna rain, but sometimes you get a nasty surprise. Rain doesn't hurt anything.

I own a business, so when i am done racing, i unload the car(5 minutes max) and put car away at work, and then upload the golf car too. Another 5 minutes. Often, i keep the trailer hooked up to a truck until next time. Drive my daily driver home.
I have this deal all figured out, my health limitations require thinking about such things. I doubt very seriously i could crawl underneath my car in an enclosed trailer to manage the tow straps. No thanks.

Most of my racing is 30 minutes away, so my needs are likely different than many who travel longer distances to race. I do generally take a portable shelter to put up for shade, sometimes use it sometimes dont.
The other races i attend out of state its always with friends and amongst friends ay Mopar events, so security is never an issue
I like being able to go home if its multiple day race locally. And if i need anything i didnt bring, i can get it next morning before racing starts on my way back to the track.
My open trailer has zero to do with nostalgia or financial reasons. Its simply the best option for me personally being able to load, unload it by myself, without help, or crawling around at my age. The tilt deck is super. Wastes less gas, and any 1/2 ton can pull it and the car/ golf cart

Yep, time to upgrade.

My 1996 24' enclosed got so bad I had to leave it in North Carolina last month after I bought a 2021 24' v-nose off a local Craigslist ad, paid $10K for it with lots of options the PO put in it. I had tried to buy a new trailer before leaving, with only two available in the northern Chicagoland area and both right at $15K with 24' and 3' v-nose. I was lucky enough that the seller in NC let me leave my old trailer at his place for a month, will go back down and fix the lights and brakes and bring it back home soon. Also the new trailers seem to be only made with OSB instead of plywood, the 2021 still had plywood. I also transport new trailers from Elkhart, IN to Right Trailer Sales in Lakeland, FL but even they are having issues purchasing new trailers...

I love the Cup holders

That is one cool trailer Rebel! I really miss my 70 VG ute, had it 7 years but I am now looking for a VE Safari, too bad they are so expensive now...