I have two girls so I can only guess what I would do, but I don't think I would paint his finger nails.  To me its just a line...just as I have lines for my girls.  There are things girls should and shouldn't do because they are girls and I feel the same way for boys.  However, I'm not going to pass judgement on anyone who disagrees and chooses to paint their sons nails :)

No, i don't see a point to it.

No I wouldn't, my husband would not like that at all! :)

Yes, I would!!!  But only if he asked of course!  I would definitely figure out an excuse to make sure it was off before school, like not letting ANY of my kids wear it to school.  My son is 8 now, and he doesn't ask anymore...but there were plenty of times he wanted painted too!  He always chose blues, greens and blacks, lol.  I want my son to be exactly what HE is meant to be, I don't want him to feel like he can't tell me what he wants and needs.

Why wouldn't I?  If he's playing with his big sister and she's painting her nails, of course I'd let him paint his, too.  Just like if she's playing dress up... I'm not going to tell him he can't play with his sister.  I grew up in a house where there were set "girl" toys and "boy" toys.  I still resent that I wasn't allowed to play with K'NEX or Legos, or get a microscope or telescope or remote control toys, because they were considered "boy" toys in my mother's eyes.  My daughter currently plays with cars/trucks and loves them.  When my son is born later this year, he'll be allowed to play with whatever toys make him happy.  I had plenty of friends who had little brothers who played with Cabbage Patch Kids dolls and had their own, and they've turned out as perfectly well-adjusted adults.

I have painted my sons toenails but not in the way I think most people are thinking. He has very brittle nails and when we trim them they crack right into the nail bed so from 2 to 4 yrs I would use the nail therapy from Sally Hansen and he ALWAYS had a clear coat or two on his toes, to keep them from breaking back too far. Now that he's older he doesn't have the problem anymore but if he asked for clear polish again I wouldn't see a problem with it.  His father freaked the first time I did it but when he saw the toenail had spilt right back through the nail bed and was red, raw and bleeding, he agreed that it was a good idea.

My son has asked while he's watched me paint his sisters' nails, however, we simply said no and he accepted it just fine. Now if he was a teen and going through a rebellious stage, I'm all for self expression.