Can you pull your Tenderly up into your truck stern first without help? If you're able to do that, it does open up possibilities for going trailerless, methinks.
I have a Passagemaker Dinghy take-apart which I transport in my pickup truck. The take-apart business, for me, is mostly about being able to store her standing up on her transom in a corner to leave room for my bride's automobile in our apartment's fine attached boathou...er, um...garage.
When we're going somewhere (the boat and I), I move the car out, get the boat down on the garage floor onto a 6'x12' piece of indoor/outdoor carpet, assemble the two sections, and then drag the rug partway out of the garage door near the end of the lowered tailgate of my GMC 2500 pickup (overkill for this, I know!), stern to stern. I then pass a bight of rope through the skeg grip, climb up into the truck bed, and lift the boat's stern up onto a second 6'x12' piece of indoor/ooutdoor carpet spread out over the tailgate and bed of the truck.
With much heaving and hoing, I then pull the dinghy up into the bed of the truck, fold a smaller piece (3'x6') of indoor/outdoor over the top of the transom, and then push the boat's stern all the way up against the front of the truck bed, leaving the nose hang out over the still-lowered tailgate. A couple of ropes passed across the gunnels from the truck's tie-down loops and then cinched down with my alpine butterfly variation of a truckers' hitch holds her in place. The gear is loaded inside the boat after she's up in the truck, to save wear and tear on the skipper. At 65, I only got so much heave-ho left in me, you see. <;-)
If we're going to launch somewhere with a regular boat ramp with a dock alongside, we'll leave the first 6'x12' indoor/outdoor carpet at home. Once at the ramp, I'll offload all the boat gear near the ramp, back down to the water, slide the boat bow-first into the water (carefully, so as not to take water over the bow), and then step off from the tailgate to the dock to tie her up so I can go park the truck.
If we're going to a ramp with no dock alongside (or if it's the off season when they've pulled the floating docks), I'll bring that extra 6'x12' piece along. At the ramp, I'll back down the ramp partway, lay that extra 6'x12' piece out onto the concrete, and then slide the boat out of the truck bed onto that. I'll slide the boat down to the water on the carpet, leapfrogging the two big pieces of carpet if needed, turn her around, and then leave her sitting on the 3'x6' piece laid about half in and half out of the water. Sort of like making an instant landing beach.
If there's no improved ramp, I'll do the same business of getting the boat out of the truck and onto a big piece of carpet and then get a "boat cart" under her to roll her down to the shore. I don't think CLC sells the one I bought any more, but what they have now looks better:
https://www.clcboats.com/shop/products/boat-gear/boat-transportation-storage-gear/clipper-kayak-canoe-and-small-boat-cart.html
The description for that claims to be able to handle 200#, so maybe that would work for your Tenderly.
In my favor for truck-hauling my PMD vs. your TD, the PMD is at least 30# lighter. In your favor, I don't reckon the bed of your truck is as back-breakingly high as is my monster GMC 2500. Mercy! My son sometimes transports our PMD in his Chevy Colorado in the same manner, and it is a piece of cake by comparison. Your TD might give you a bit of trouble balancing her on her pointy forefoot whilst you lift the stern, whereas my PMD carries her flat bottom all the way up to the transom. You'd just have to try it and see.
Not having to fool with a trailer, especially not having to store the boat on a trailer, is what makes having a fairly substantial sailing dinghy like this possible for me. The indoor/outdoor carpet is the key to making the whole thing work without tearing up the boat and without ever having to lift the entire boat all at once.
May the Brute Force be with you, but not the Blunt Force Trauma!
.....Michael