I'm glad to hear that things are settling down emotionally. You'll know what is right. Listen to your heart and mind.  Â
Â
One thing about socialization and toddlers - (esp. for only children), I personally think it's good to have peer interaction. Cooperative play is not the be all end all to wait for a certain age. There is a tangent between parallel play and cooperative play - it's called: "age appropriate interaction" or "bickering" or "fighting" I don't think it's so much a "pecking order" as spirited interaction, learn about success, sharing, failure - A bit of struggle/competition can be a good thing. And, toddlers struggle and compete. I speak from the perspective of a parent of a wonderful "only child" - 3 yo girl. From a very young age, she's been at the same babysitter - she started at 2 mo. My beloved babysitter seems to adopt an infant, raise them to crawl/walk (limit of 3-4 total), then bring another. Now Lindsey, my little one, has a 2 1/2 yo boy (1 year younger than herself) that she has literally grown up with. They fight, bicker - in fact, even today, when I went to pick her up, the sitter shared a few funny stories. Lindsey and her buddy were bickering - babysitter said (very nicely): I don't want to hear about it unless there is blood" Lindsey pointed to her toe which had a "boo boo" (unrelated to their bickering). De-escalated the whole situation and the kids laughed. So, I do think stimulating, even competitive interaction between young children is good, especially for "only" children. She competes with these other children, sometimes wins and sometimes loses. Not in a bad way, just more as one would with siblings (or other cubs in a pack). Compete is probably the wrong term (Not trying to raise a competitive child - far from it. I just want my daughter to know she is loved and there are time she won't always get what she wants). Another girl, about 8 months older - these girls are feisty in competition, but great friends. If one wants the toy, the other one wants the toy. They settle their differences.
Â
If you do enroll him, let your son be the guide. If he wants to attend, let him. If he wants to stay home, let him. You may be surprised - he might be more ready to separate than you.Â
Â
I drafted a few other comments, but realized they were more geared to traditionally Montessori "drop off" and "parental visits" that may not apply to your little one. I'll save those for another thread so as not to derail your topic.
Â
You'll make the right decision - sounds like you have an amazing, precocious son. Cherish and enjoy - and then let him go (when the time is right - maybe this year, maybe next year).
Â
Re: being sad...sigh - my babysitter was telling me that my daughter's senior child (he's 2 years older, and was her mentor from when she was an infant) is starting kindergarten and commented that his mother would be in tears seeing him go to school. Me - I'm thrilled my 3 yo will go to school - tears come to my eyes at the thought she doesn't want to go "nudie butt". I can deal with her being in school, but the thought of the (not too distant future) day she doesn't want to rip off her clothes in merriment and dance around the house, that is the day I cry.