I have both H&H and Titan trailers. My H&Hs are 24' electric tilt, 14K bumper pull and 3.5K 5x10 tilt bed and 18' cargo trailer. My Titans are 31', flip up dovetail, deck over with dual tandem axles, 25K gooseneck and a 14', 14K, bumper pull dump trailer. Titan is made in KS and H&H in IA.
I am not brand specific and have owned other brands. Both brands have served me well. I do think the paint on the H&H 24' trailer is subpar compared to some other trailers I have had but it does see more road time and gravel. My H&H 24' tilt has torsion axles. I love them compared to spring axles on the heavier rated trailers. An empty, 14K rated trailer with 80 psi in the tires can ride rough. I had originally bought a H&H, 22', 14K trailer with springs and flip up ramps. Returned it in 1 week and decided to get the 24' electric tilt with dexter torsion axles. Both trailers weighed about the same but the ride of the torsion axles were superior empty or loaded.
I will say H&H 14k trailers are well made. My 24' has 8" channel frame and 3" channel crossmembers every 14". (I think the 20' version use 6" channel iron frame with same crossmember spacing.) Some trailers have 3" channel crossmembers but as far as 24" spacing. The crossmembers are sprayed with an undercoating. Most companies don't even paint them. The H&H wood decks are the best I have ever seen. The wood is pressed together tightly in place when laid and the wood is reasonably dry when laid. There is almost no gaps between the boards. You will not find a tigher deck.
I helped my brother in law put a new wood deck on once. Got the new pressure treated wood, pressed it on tightly (even used clamps) and it looked great. I saw it 2 months later and could not believe the gaps between the boards. Definitely pays to let the wood dry before putting it on.
Trailers are not rocket science. You kind of get what you pay for. Heavier frames, torsion axles, led lights, jacks, deck overs, fenders, type of ramps and other options all affect the price. If you are not in a hurry, have your trailer custom ordered to your specs. I did this with my H&H trailer. H&H has a vast number of options available. Took about 6-8 weeks to get my trailer. My dealer is one of or maybe the biggest H&H dealer in the US. His entire business is selling just H&H trailers. He has as many as 200 trailers on his lot and no haggle, fair pricing. He is located about 6 hours from the Twin Cities. The name is Neil's Trailer Outlet. Ask for Dick the owner. Even if you just want to check prices compared to other H&H dealers. He could probably even fax you a base price list and options list if you are interested.
P.S. Used to live in Rochester, MN. Never could get used to those winters.