I would look at what the rental houses use- tilt/drop tail single drop tandems. They usually rotate their fleets quite frequently, but their trailers get used hard. Lots of loading and unloading cycles, rough in town use. Short wheel base truck and as short of trailer as you can (40-45'), crowded streets are no fun with a 53' double drop.
There are a couple of guys on here with some fancy dropped, stretched trucks with sleepers. Chrome bumpers 1" off the ground. I can appreciate the time they've put into them, I just don't think they serve a useful purpose in the construction game. I sure wouldn't want to make downtown deliveries with one. I have a hard enough time with short wheelbase daycabs in my area, those dropped bumpers would be ripped off in a heartbeat in my use, and I prefer the visibility of a daycab.
I own a sliding axle tilt deck trailer that I got from a asphalt paving company for moving my straight mast forklifts, I also use it when I rent a telehandler. The axles slide ahead and the whole bed tilts, makes it have a nice low loading angle. The only downside is if the parking brake of what you're loading doesn't hold well, you better have someone with you to tilt the trailer back flat, or you have to winch it on the trailer (which is also a two man job). I would take into consideration your current/ future equipment plans when picking out a trailer. You could get by with a single drop lowboy with just ramps and load a telehandler, but if you've got manlifts or similar things to haul, it wouldn't be as handy.
I pull my sliding axle trailer with a tandem international, cummins, m11 (330 hp), 10 speed. I have a western star tandem, detroit 60 series (500hp), 13 speed, that I pull a double drop triple axle (50 ton trailer), and its a much better tractor than the international. The M11 is fine up to about 70,000 gross, 80,000 in flat country. The cab and construction is just much better on the western star, in addition to the more hp. Mine are both 90's versions.
Peterbilt, Kenworth, western star, are kind of top of the line over the road trucks, that also make day cab versions. Should be lots of macks out east by you, they used to dominate the construction/ day use category. I would tend to put macks and the older ford 9000, in the day use, less fancy, but tough trucks category (I own one of each). Not a big fan of freightliners, international, or volvo. Cat (3406), cummins (big cam/ n-14), or detroit 60 (12.7) series engine (they're all good motors) mack would most likely be mack engine (not always, but they're not bad motors in mid 90's), 9 or 13/15 speed, 3.90 to 4.88 rear ratios. I prefer older over newer, pre 2003 gets you earlier than most emissions problem motors. Plus if you need interstate authority, pre 2000 doesn't need the new electronic logs.
In my area $15,000-20,000 will buy you a decent mid 90's to early 2000s, daycab. It will take about that same amount to buy a decent trailer. Neither would be perfect at that price, both needing a little work (deck boards or brakes on a trailer, tires, lights, maybe a clutch or trans maybe injector on a truck), but usable with a little work.
I'm not a big fan of my tall chrome stacks on my western star, I'm just too cheap to change them out (were on it when I bought it). The international will turn shorter (less wheelbase), but it shakes and rattles a lot more going down the road. They are both air ride.
The second picture shows my tilt trailer a little better, it pivots right at the drop, the axles slide ahead and there's a little back ramp that is hydraulic. It's a trail-eze, landoll makes something real similar. They are heavier and more complicated (more $) than a rear tilt ramp, which is why most rental outfits don't use them. Once in a while the sliding axles is really nice getting around a tight corner.
