I have always had a 'benign neglect' mentality towards DS1 (5.5yo) although I didn't realise there was a name for it! He has always had a free reign to crawl/run/jump around the place, with stairgates to barricade unsafe areas when he was too young to understand why he couldn't go somewhere.
We live in a cul-de-sac and our house is away from the road - there are several paths and a grassed playing area that are accessed without going on the road. For the last few months, he has been allowed to go out to play on these areas with 2 other boys. I spent the first few times peering out of the window until I was satisfied he wasn't going in the road (he never has) and now I just keep an ear out for any shouting.
HOWEVER - I now feel incredibly guilty because at the weekend he broke his arm when playing unsupervised in the enclosed garden of one of the other boys!!. Poor little mite came staggering home crying, holding his arm after he said he tripped and fell on a scooter. He needed an operation and now faces the whole summer hols with an arm in plaster.
Logically, I know that it is not my fault - he was playing in a safe, walled garden to a house with adults in. There were 4 other kids present, including a girl of about 13. He tripped and fell on a toy - which he has done countless times at home. He was about 20 metres away from me, several doors down the road. It was bad luck, nothing more. Still, I felt SO bad last night when he was crying 'cos his arm hurt and he couldn't sleep.......
I am hoping that this doesn't stop me letting him explore and grow his indpendence. Obviously at 5 years old he isn't left anywhere on his own and won't be for some time. He never plays out on his own either, only with the other child(ren). He knows not to try and cross roads etc and has been heard telling the other boy off for playing in the road and for leaving his toys on the path where other people could trip up .
We are lucky that our local environment is very child friendly and neighbours all keep an eye on each others' kids (half the street came over yesterday to check he was OK), but I am having a hard time letting him out of my sight at the moment.
Sorry, this turned into a long 'poor me' post, didn't it?