Question about 2290 for new plates in CT

Check to see if previous owner paid the 2290. It stays with the truck, not the owner, so if they paid it all you need is a copy of the reciept and you're good to go.

 

Ct Irp unit won't register a truck with apportioned plates without a paid stamped 2290. And a PILE of other paperwork. You'll also need a signed by both parties contract with explicit information regarding you working for whomever has the authority you're operating under. Bobtail physical damage for temp plates-as far as I recall the insurance company will give you the minimums, as you had to pay in for ct's minimum in addition to "uninsured/underinsured motorist" coverage that ct requires.
Plates are about what you're expecting....but change depending on what states you run and how much you run in them. Mine were $1380 something this past year, high $1700s last year: bc I removed a couple states I hadn't been running in.

 

WRONG! That was the way it was maybe a decade ago, but its followed the owner for quite a few years. The last owner's 2290 means nothing to the current owner.

OP, some states will allow initial registration without a 2290, as the IRS gives you 60 days to from the purchase to pay it. Since you are very late in the year, you'll pay a small percentage of the 550. Your local IRS office will figure out your tax and give you a stamped copy for your plates. As far as insurance goes, bobtail insurance can only be bought for a leased on truck. OOIDA has an easy to get policy for what you need.