Hi there,
my first baby was touchy
what you describe sounds totally normal for a touchy baby!
PU/PD would not have worked with him, I ended up using sh/pat and doing a very gradual transition to the cot. He wouldn't have settled initially in the cot - hysterical would definitely have been the word. (Even as a tiny baby he wouldn't go in a pram for example, totally hysterical). I should say he learned to be a fantastic sleeper and still is (touch wood) very reliable at 5yo. The thing with touchies is that they are sensitive to OT and OS but they tend to thrive on a good routine, so keep watching him and you'll get closer to learning what his ideal A time is. I would suggest making sure that activity right before naps is very quiet, that may help you.
I started teaching LO1 to sleep at a younger age but what I ended up doing was sh-patting him in my arms until very sleepy, and then transferring very gently into the cot and keeping shushing/patting in the cot until he was deeply asleep. Then he was usually set for a good nap
Remember you can tweak the sh-pat to a rub/hum or whatever works for LO, because he's older, he might prefer less shushing, depends on him! But since he's touchy, it might be that physical contact will help him to relax and get ready to sleep. So hold him, snuggle him, keep it very low key, help him relaaaaax and into the cot. Or, as Buntybear says above, you can try him with lots of contact in the cot. So start with the big sleepy snuggle, then transfer into the cot (you may want to bend into the cot to minimise the time he's not being held) and then firmly keep contact with him, so he knows you're there. For now, don't bet on putting him down and walking away.
Don't feel bad about feeding him to sleep! Happens to us all, and was the best strategy at that moment. What you know now is that you have a secret weapon for if/when things go completely pear-shaped. It's called APOPing - accidental parenting on purpose - when you need to
Another thing that can work well for touchies is a sling nap.