So an update from us:
We think we've weaned him off the hand holding with two tactics - firstly getting him tired enough that he doesn't try for too long; will give up after a couple of attempts and then cuddle one of his (numerous) teddies. Second is we will now stroke his foot when he's reaching for hands as it seems a bit easier to withdraw! Although he picked on this quick time and will now ask for 'toe! toe! toe!'. The longer winddown definitely works well and gives him the cuddles he needs outside the cot. Don't think the darkness is an issue as the room isn't blackout and actually fairly light at bedtime.
The nap is still shrinking - this weekend we had:
Fri
WU 6.30
S 12.45-1.25
BT 7
Sat
WU 6
S 11:30-12:15
BT 6.45
Sunday
WU 6
S 3-4!!! I tried putting him down at 12.30 after he was rubbing his eyes but he just rolled around singing to himself and generally larking about and by 1pm he was giggling at me so gave up! Finally dropped off at 3pm!
BT 8-6.30
So short naps 3 days in a row and I wasn't convinced he'd make it to bedtime each day but it was actually great as he was actually tired and ready to go down at 6.30-6.45 and took less than 5 minutes to go to sleep and then he slept straight through, no wake ups!!!
By comparison he was at nursery today (he's there Mon-Wed) and he slept 12.25-1.40 and as I write this at 19.15 he is nowhere near tired! Will try him down again at 7.30 and see how we go but will be interesting to see how well he sleeps tonight. I think we might need to cap that nap at nursery (we never need to at home, guess he gets more stimulation at nursery!)
He has always generally been on the low side and it's often taken a big push in A times - I remember we had the dreaded 45 min nap at around 6 months and it was only through encouragement on here I pushed his A times and we got the two glorious 2-hour naps per day at 7 months
Then we were on one nap by 11 months so I guess both transitions those were a little earlier than most?