Hi there,
good ideas from Fleur
I was going to add, if there is always resistance at nap time, then he might be UT. Do you think he might be due an increase in A time? Is it a while since he's had one? If you go for an increase, just add 10-15mins and keep it at the new time for three-four days to see how he adjusts.
As for waiting to see if he self-settles, the rule of thumb here is of course to listen carefully - if it's an 'I need you' cry go directly in, don't wait. If he's just sort of talking to himself, let him continue for as long as he needs.
Am I asking for too much from an 8 month old?
No it's certainly possible
doesn't always happen mind you
and definitely if his routine is off that won't help. I think you can't go wrong if you read that link Fleur gave you, and also listen to your baby. He will always have periods of needing you more or less, and settling on his own is something he needs to learn with you helping him, so it can be a gradual thing, yk?