So much sympathy. I still feel like I can't escape bedtime! Like last night, the girls have colds. My oldest, the most demanding one, is a bear when she has a cold and always has been. She screeches and screams when she gets clogged up--a real pain in the family bed. So, last night, I just put on my PJs, brushed my teeth and went to bed. Damn! We just got the next season of Grey's Anatomy from the library, but I knew that if I got my expectations up to watch it, not only would I be interrupted by her waking up, but I would feel spiteful to boot. Tonight I think I'll get out.
I don't cuddle with my girls so much (because there are 2, one on each side, and rivalry is alive and well in our house) but just lie there, hold hands, massage a aching leg, whatever. They want me to sing. We've been doing "last words" in the dark room and that has been a sweet time, but I have to watch it or it wakes them up more than makes them sleepy. It is the only time where we can really chat about whatever.
Sounds like fixing (and nixing) the daytime naps might at least give you a leg up. It sounds like there are other issues besides naps, but at least that will make her sleepier and easier to coax into sleep.
When we did the transition, bedtime began absurdly early-- 5:30 to start storytime, lights out an hour or so later. We were able to slowly move that start time back to a more reasonable time. I think for a couple years we started the process at 6:30. Now we've been starting at 7:00 since Daylight Savings ended, back from 7:30 which we had been doing (but I was emerging too late in the evening to do much of anything but get ready for bed.)
Good luck on this. Realize, she can't make herself go to sleep. I have gotten grumbly and angry so many times in the last few years I can't even keep track. And I know it does not help one bit, but sometimes? There I am getting angry again. It helps so much to adjust my expectations. I actually get ready for bed so I can let myself fall asleep sometimes. Before too long, I am out on the couch, cuddling with dh and getting to the rest of Grey's Anatomy.