Nap transition or overtired?

[GGS01]

My 10 month old baby boy has suddenly decided to take 2 naps during the day. His naps can be anywhere between 30 mins and 1.5 hrs. His second nap normally doesn't go beyond 4:30 pm. When he was taking 3 naps, he had his dinner between 7 and 7:30 pm, a bath and then to bed by 8:15pm. He feeds to sleep and is usually asleep between 9pm and 9:30 pm. Ever since he dropped his third nap, he is too tired by 8 pm and sleeps before 9pm. But then wakes up at around 12:30 am and wants to play. We co-sleep because he is a terrible sleeper and wakes up 5 to 7 times all night long. This mean no one gets to sleep for an hour or so.

Should I force him to take a nap around 7pm and then bed by 9:30 pm or let him sleep by 8:30 pm and hope he gets the hang of it eventually and stops wanting to play at 12:30 am?

We just moved bedtime earlier and had to deal with the wake ups and the earlier morning get up for a few weeks.

My son has never slept well. He is 8 months old and wakes constantly. He has took to getting up for two hours between 1 and 3 am as well as wingeing constantly in sleep. Everyone says it gets better, but it keeps getting worse. Now his day time naps are only half hour long. Anyone got advice. I'm so down from no sleep and I'm restarting work soon

@Sleepyjanealways, my son also had 30 min naps till he turned 10 months old. I am not sure if it became longer on it's own or it was because we went on a vacation and were able to extend his naps by holding him after 30 mins, patting, shushing etc. Even now he needs a pat after 30 mins every nap but he can sometimes do up to 1.5 hr. As to sleeping at night, he has become worse. He wakes up 5 to 6 times now. Am hoping it is just the 10 month regression and passes soon.