https://babywhispererforums.com/index.php?topic=113115.0Here is a link to people's experiences with the transition. I think it is time bc it is a big safety concern. Even if he is adept at getting in and out, you don't ever want to ever have "that moment" when something goes wrong. A friend on BW told me that her cot came with a safety label that states to move out of the crib when they start to climb out. Our crib was convertible, so we just took down a side and put up the half railing.
He is probably undertired for his nap. I would move the nap to 1:30 to start, see how he does. If he still messes about, try 1:45. Then 2:00. My son has a longer A time in the morning than yours but typically 2yo need at least 6 hours of activity before nap. I would also suggest a very active activity for him daily. I have many friends with truly active kids that need intense physical activity to help release their energy and be tired enough for sleep. Also typical around this age is the decrease in amount of daytime sleep... In your case, I would try the later naptime and cap nap at 1 hr. to preserve bedtime at 8:30.
As for keeping him in bed, it's a matter of consistency and reinforcement of your routine. And perhaps for him a reward system. Have you used a sticker chart before> A simple grid with 4 in a row or so, where for every time he stays in bed 5 times in a row, he gets a special treat- 15 min of tv, a small new ball at the store, an extra book at bedtime, etc...
How is potty training going? These are big changes so if you feel there isn't progress with PT, consider waiting until he settles with the big bed and naps. If he's doing well, by all means keep going! Just so you know, sometimes they regress when switching to a big boy bed... it should be temporary.
