If you are in SE Wisconsin, Tom's Trailers on the NW side of Milwaukee will set you up properly. I've dealt with him a few times, fair, good stuff.
The Corral out of Sullivan, Wisconsin, new and used trailers, generational family business, nice folks, good equipment.
PJ trailers near Johnson Creek, at hwy 26/ Interstate 94, they build, sell retail and wholesale to many other trailer retailers.
There are tons of others, pick up a copy of Auto/RV next time you are at the gas station, its a free weekly publication, and has plenty of ads in the back with dealers and private sellers in the state. Lot of options to choose from without going to big box store, which lacks the follow up support you may need or the trade in capability when you realize its time to upgrade.
Keep in mind, Wisconsin requires registration on trailers exceeding #1500 gvwr.
Also, call your auto insurance carrier, it needs to be an additional item on the policy.
Electric brakes are a wonderful thing, and make for a great item at resale or trade in time. And the brake controller in the vehicle then allows you to use any trailer with brakes and even better, rent a trailer that will have brakes for the occasional heavy load.
Renting a flat 16' trailer, 10,000# gvw only costs $50-$60/day, great way to handle that occasional oversize load, and just buy what you need for the majority of your needs.
Good luck, lot of deals out there.
PS.. Have to agree with the tandem axle choice folks are talking about, and it really sunk in for me when my 83yr old dad was commenting on his first one for hauling wood and his Ford 8n tractor around, he wished he'd bought a tandem axle 40yrs sooner.
BUT, it depends on what you have for a tow vehicle, space to park it when not in use, budget, and other details only you are aware of.