N.P.
Hi C.!
Yep, it sounds like you need a new sleep routine. One for his naps, and another for bedtime. Not every baby goes right down to sleep, and if I had to guess, I would think your son is in the majority of fighting it :o)
He needs to be more active during the morning, then maybe go do any errands with you to 'soothe" him on the way home. Hopefully naps with be easier and the more comfortable he gets, the longer they should get.
Your bedtime routine, is probably the most important, because it sets the "stage" for his llittle young life and school. The earlier you start your bedtime, the better.
At his age, he really should be in bed by 7-7:30 to sleep almost 11-12 hours.
It takes ahwile to get him "on routine", but if you do things in the same order, then he will get it, and bedtime/nap will be easier. Even setting the microwave timer for certain things (to be done) so he hears a "beep".
When you are putting him down, LOVE HIM with gentle rubs, etc.... then say "oops! I forgot to do....I'll be right back"............then come back within 1-2 minutes to earn his trust that you are always right there for him. Then after soothing him with a couple more "pats", then "OH know! I forgot to ......" ....The first 3 nights and the first 3 times each night, you should return within 2 minutes. After that, you can stretch it out until 4ish.
I would always leave his door open, at least half-way. He will eventually fall asleep waiting & KNOWING you are coming back.
I hope this works for you. It worked/works for me. I'm at the point where I can go back in every 5-10 minutes now :o) It takes alot of effort on my part, as the mommy, but I don't want the tears for things like this. Doing it this way, at least he's in his own bed, and I'm not laying with him, and there are not any tears :o)
Good luck, C.!
~N. :o)