RBB wrote:...
My concern is the process of applying for VIN and getting it registered... unfortunately, I no longer have WI plates (no plate required for trailers under 3000lbs!)

so eventually, I am going to need to go through the process of getting plates in IL... not looking forward to that process...
My concern is the inspection, and how much they care to look at these points...
Sorry, off topic but thought I would pass on some Wisconsin registration info...
RBB, you probably know this so don't be offended. I'm just passing this info on for other WI residents that may want to register their TD since they travel out of state. In Wisconsin you
CAN register an RV, boat trailer, whatever, even if it is below 3000#. I have done it twice, first on my Woodie TD and now on my Foamie TD. It's not cheap... about $167 for a title (if you need a replacement it is less $) and $15 for one year registration. In an odd quirk of the WI-DMV rules, if you have a utility trailer and you want it registered it is $167 plus $50/year.
Four of the following six items are required to qualify for registering as an RV. They do allow home made campers. And, I don't know what WI's definition of "Self Contained" is. I know what most people would think it is but couldn't get the nice young lady at the Green Bay DMV to come up with an answer. She was very helpful so I didn't push her to find out as It didn't matter. I met five of the six. Anyway, this applies to Wisconsin registration of a homebuilt camper. Not nationwide.
-Water supply including faucet and sink (yes, I'm calling my 2 gallon water jug with a valve a "water supply" Good enough for WI-DMV)
-Cooking facilities (yes, I'm calling my little one burner Coleman type butane stove a "cooking facility")
-lce box/refrigeration (yes, I have a 12v fridge)
-Self contained (Whatever that is. The Big Box RV crowd undoubtedly would disagree with this. I won't bore you with the story of an online camping reservation service that refused to allow me in "their" campgrounds without a toilet and shower in the camper)
-110/125v electrical supply (yup)
-Space heating and/or A/C system (1500 watt space heater I've never used but its in there)