ICO player count doesn't get above 200 very often anymore....that being said, every time there's a sale you might get a peak...but in general, the ICO online counts are low, and most of those people are just comp stomps with friends....
You cannot reconnect to matches you've lost connection to...it is a "no-brainer" feature for games made today, but sins is old and wasn't made at a time where that was necessarily expected...implementing such functionality probably would require massive rewrites to game code...they may implement it but I highly doubt it....
As far as I know, MDs are still a problem....there have been worst times, but it's not a rarity like you'd hope it to be....
