Isle of Skye

Taking a look at lodging availability on booking.com (you don't have to book through that website) for the first vs. second weekend in June might give you an idea. However, Skye is extremely popular and has insufficient lodging capacity to meet the demand. I think from that standpoint the situation just varies between challenging and really difficult--and potentially impossible if you won't have a rental car and need a place with public-transportation access.

Weekend or weekday it won't really make a different in terms of how busy Skye is. It's busy all season and really all year round. Get your accommodation booked as soon as you can, but bear in mind that some small B&Bs don't open their diaries until Christmas or the New Year.

As Skyegirl said, it will make no difference. Just book lodging as soon as rooms open up. And plan to book restaurants for dinner or Sunday lunch ahead of time.

The crowds will be basically the same throughout the season. Try to start your touring early in the day to see at least some of the highlights without fighting for a parking place.