Getting my rabbit to tolerate being held

I have never met a rabbit who loved being held, haha. My first rabbit, Clover, absolutely hated it. She would have to be restrained by another person when it came to nail clipping time, and when I had to move her to the carrier or her cage she scratched me up. I think at one point I had to superglue a flap of skin back on!
Chestnut I have held since she was 8 weeks (when I got her) once a week until she was 6-7 months old. Now she lets me hold her and clip her nails, but she still puts up a slight fight. She doesn't scratch hard or bite, so that is a plus.
for my newest bun I have decided to take another approach and hold him for about 5 minutes two times a day. He is 5 weeks so I hope if I do that for a month, then once a day for six months, then once a week after. I hope he gets used to it. He is going to be a big bun so I definitely want to get him trained, haha.
For car rides, I like to keep them in the kennel in a dark area. I find them more comfy that way, but there are several methods of course.

Thank you! I expect he won't ever enjoy being held, but I just really want him to tolerate it and not be SCARED when I do hold him. I've only been picking him up for about 2 weeks now and for only a few seconds to a minute or 2 every time and I've already seen imrovement. The car is where he lets me cuddle him the most which is why I really enjoy being in the car with him. Hopefully holding him for longer periods in the car will get him used to it in general! That's what I'm hoping anyway lol

Treats are good but be careful giving wheat or bananas.

Anything sugary can rot their teeth and then you're in for teeth surgeries which are expensive and not fun for anyone.

Yes, hold as much as possible. Best way to get a rabbit to trust you is to lie on then floor and let him hop around you. You could be holding a treat. Or sleep with him. But eventually start holding him once a day. You'll need to be able to do this when he is older or ill or for grooming. Wear sleeves and gardening gloves if necessary. Let him express his anger on a piece of paper.

I also like to pet the bunny while in the carrier in the car. I do think carrier needs a seat belt on. A loose bunny could be bad in an accident.

The more and more frequently you can hold him, the better. I've had great luck with rabbits, apparently, since all mine have loved being held. Mind you, I got one from a school when I was in my teens, and then another from a friend who could no longer keep him. Both of those rabbits were love and contact addicts. I have a new lion head/Netherland dwarf cross now, and after a little over a month, she does the flop across my lap when she can figure out which position/angle she wants her bod to be as she zones out to my constant stroking. She also gives tons of licks, as has every other rabbit I've owned. And from the day she arrived, I held her for short periods at the beginning, but very frequently after about the first day of her being here. And the periods of time have lengthened to where I can watch TV with other people around, and Felicity blissed out on my lap, or in my arms.

But the most trouble I've had with rabbits is going up and down stairs while holding them. They hate the motion/sight, something about that can make them suddenly anxious. Butterflies in stomach, maybe?

I also cover Felicity's eyes when about to pick her up, she recognizes my hand over her head as comforting. She relaxes that way and doesn't kick out and just lets me pick her up. Putting her down is another thing, I've noticed most rabbits seem to want to scramble/run/jump as they are being lowered to the ground. Only my first rabbit, a Dutch, eventually outgrew that and just behaved like a rag doll cat no matter what I did with him.

Felicity gets lots of pets on the head and neck, especially after she grooms me or whenever she seems to be a little excited or anxious. She got a lot of hand above/stroking head to get her into settling on my lap. The very first time I tried to put her on my lap, she climbed back up my front, wanting back in my arms instead.

Something else she does that is just adorable is to stand up on her hind legs at the corner of the cage when she knows I'm coming for her. It is not the corner furthest away from me, it's the one I am approaching. She stands and stretches herself up as tall as she can manage, to greet my hand with sniffing and licking before I can even get it into the cage.

In the cage, she just stands/sits/lies there whenever I stroke her, unless she wants to have a lick attack, then she licks the heck out of my hand/arm. My Dutch was the same way.

If they can get that affectionate from in the cage, there's probably a good chance they may eventually carry that over into being held in your arms or on your lap too.

And in my experiences with hands on at any pet shop, I've always found that of all the small animals, rabbits and ferrets were the friendliest towards me, a stranger to them.

I can groom Felicity when she's relaxing on my lap, but haven't ventured the nail clipping yet. That's something I'll need someone else's help with because I'm terrified of clipping too much.

It sounds like you're doing amazingly well with him in the car, and taking that into consideration plus the small improvements at home, it sounds like you're doing everything right. Just keep it up, and the more relaxed her gets, the more frequently and longer you can hold him. Whatever you are doing to make him relax when he's with you, just keep doing it. And if he licks you, keep up the stroking and any encouragement. Purring, licking and sprawling out on or near you are all signs your rabbit feels safe around you, and licks are a sign of love. So just keep doing what you can to make yourself a very pleasant experience for him and take note of any and all small improvements. His mood might vary from time to time so that he seems more relaxed one time, and not so much the next.

Also, if you ever let him loose in the house, he could be confused about this being held thing, associating being out of the cage with play time.

I had a Dutch that had learned to sit tight on my knee when I took him in from the outdoor cage going into my house. He had to sit still while I took off my shoes. He lay on a chair or on my lap when I watched TV or just brought him in for my friends.

But I had an old playhouse in the back yard at that time, before it was converted into a tool shed. That was where he got his running loose play time. So when I took him in there, he didn't wait for me to get my shoes off, but hopped off my lap as soon as I crouched down to untie my shoes and put him down. Rabbits can really surprise you with their intelligence when they are so well bonded with you.

Hope you have the best of luck with your rabbit and holding.