Lisa
I agree with Laura about the daily routine needing some adjustment. Ideally you want your LO on a 12 hour schedule, so waking @ 7-7:30, or 8am with a bed time 12 hours later. @ 14 months old your LO has progressed nicely to a one nap a day schedule which is great! I would strongly urge a 7-7:30 bed time.
So your day would look something like this:
7-7:30am Wake for the day
E & A time from 7:30- 12:45
1pm - 3pm Nap
3:15 Snack
3:15 - 5:20 Active play - lots of energy being exerted, try to avoid TV time
5:30 - 6 Dinner time
6 - 7pm - Bed time stories, wind down time a calm bath and massage, Pj's
7-7:30 Bed time
If you're willing to stick it out, it'll take you approx 7 days to get your LO back on a routine that you'll be much happier with - and one where he'll be in his room. @ around 14-15 months my LO put up fight about her crib and refused to sleep in it, so we switched to a big girl bed. The transition was smooth and worked well for us, but try to get back into his crib.
The key is absolute consistency from all parties involved. If you can deal with 7 days, and a few hiccups, you'll make it!!
Try watching his drowsiness/fussy- ness around nap time and carry him into his room with his comfort items. Lay him in his crib, rest your hand on his back and remove it as soon as he's calm. Walk out. If he erupts, go back in and do PD, don't take him out of his crib @ al!! Place him back down (eyes away from you, ideally on his tummy) and keep your hand on his back until he calms down again. At first, you might have to do this for the entire nap time, but by day 3 - you should be good to go and you'll take the next 4 days to simply make the transition final. You'll also find the further into the process you get the less you have to reassure him that you're there - so by all means remove your hand gradually earlier and earlier. I promise, it works!! Just stick with it!
Sending you hugs, strength & courage!!