Hi D.!
First, let me share my information... I have 4 children. A son- 9, a daughter-almost 5, and a set of twins boy/girl -3. Being an older parent (I'm 41 now) I've learned alot over the years watching my friends raising their kids. I am not an expert by any means, but I must say, in all my experience, consistency is critical. This is a typical evening at our house: We eat dinner every night at 6:00 and as soon as dinner is over, bathtime, a short story and then bedtime. We try to keep it calm during bathtime. After bath, we get into our warm pajama's and we dry their hair. The kids get into their beds and the lights are turned down a bit. We read a short story and say our prayers. The lights are out and our children (all of them) are asleep by 7:30. (It is very rare that they get out of their beds for any reason). Guess what! Now mom and dad get to wind down with one another! We get to talk about the day, watch a movie, check our email if needed, or whatever else we choose to do! YEA! We get to reconnect as the couple that we are! Our children are awake around 7:00am and we go at it again. Our children are pleasant to be around because they are rested and structured. My twins still take a nap every afternoon after lunch for about an hour- Their naptime has shortened as they've grown.
Children, like adults, thrive on a schedule. I see a lot of inconsistency in your son's routine. Also, I think that your sons inability to sleep is due, in part to his lack of rest, and I believe that your son's lack of rest is due, in part to the methods (wrestling and playing) that you are using to prepare him for rest. This may sound harsh- it's not my intent- but you need to be the mom. It's your job to help get your son on a routine. He is not mature enough to "set his own schedule". It is very important for a child to have an appropriate amount of rest. For a 2 year old, the appropriate amount is around 12 consecutive hours, give or take an hour. When it is time for sleep, begin setting the environment for sleep. It's a good idea for a nap as soon as lunch is over because he's had 30 minutes or so without vigorous activity so his mind is calm and his heartrate is slower, which will aid in rest. If you are playing with him or wrestling with him before bedtime or nap, his mind will be full of activity and his heart rate elevated which will take an hour or more to calm down-hence the tossing and turning you've observed and mentioned. TV time before bed should also be discouraged as the activity on TV will get his mind in a thinking process rather than winding down to a resting mode.
I do not recall seeing the age of your other son mentioned in your post, but his schedule is important, too. If he's pre-school age, he should be in bed befor 8:00. If he's below the age of 14, he should be in bed before 8:30 or 9:00. Kids who are allowed to stay up until "they" decide they are tired have poor study habits and generally don't do as well in school. The change for your family will be hard to embrace, but the routine will be adapted within a week if you remain consistent. The rewards will be reaped by everyone!
I apologize for being so wordy and I do hope I have not come across as critical or judgemental. I just wanted to share in hopes that you can adapt some of these things. I know it will help all of you, together, be a happier family.