Actually all of our trailers are registered,about 17 bucks a year. Fla. bases the cost of registering a trailer on it's empty weight. Trailers 2000 lbs. and up are titled as well as registered. Like a car.
What I do here and what might work for you guys having trouble getting your trailers registered is tell them it's a homemade trailer. I've never had a problem doing it this way.
In MD all trailers are both titled and registered. If a trailer comes in from out of state, they look it up in a book to see if it's a title state or not. If not, then there's other requirements - a notarized bill of sale, and a registration if it's a registration state. If you don't have the requirements met, you need to go back to the seller and have them come up with the paperwork, not always an option. The other option is to put everything you have together and petition the courts to award you ownership. I haven't tried that one yet, sounds like a pain.
I'll be going through all this with my Corsair trailer - the boat came from Sarasota, and the previous owner kept it a yacht club and never registered it. I have a notarized bill of sale, but no registration. If I can't title it, I may have to trash it or sell to somebody out of state. Fortunately it's on its last legs anyway.
On the homebuilt thing - we've some good and bad luck on that one. They've started to catch on and require a visual inspection (by State Police) of the trailer to verify its homebuilt status.
My worst one was when I bought my Hobie-20. It came from Connecticut, a non-title state. But the fellow I bought it from was moving to Illinois, a title state. Somewhere on the paperwork he put his new Illinois address, and that was it - I couldn't title the trailer until I had an Illinois title in hand. No form of logic worked. I ended up selling the boat and trailer to a friend who sold the trailer to his father in a non-title state for $1. His dad registered it there, and then in the end it was transfered to Virginia using the new out of state registration and a bill of sale back. All this for a boat trailer...
The funny thing is that all this crap just encourages people to find ways to circumvent the law. The intent to make sure they collect tax on title transfers. But it's such a pain that people end up using one tag on multiple trailers and such, borrowing a tag when they need to move a boat, or not ever titling and registering a trailer if it's not going to see road use. In those cases, the state gets no tax money.
Here, boats without motors need no titles or registration. Although I can see their desire for tax revenue to help upkeep waterways and such, I hope they never start with the titles and registration on non-motorized boats - too many boats have neither and if they don't properly grandfather them in it will be a nightmare trying to sell or buy a boat.
Also in MD, for boats that do get titled and registered, there is a 30 day period for completing that paperwork. If you don't do it within that period you get fines added to the tax. This was done because they found people were keeping their boats under other state's registration to avoid the sales/transfer tax.