Contests depend on skill—I’ve won some writing contests, some speaking/oral interpretation contests, and, once, a dance contest.
Raffles and drawings are chance, but you can up your chances even if you only enter once, if it’s the kind of drawing where you get to personally drop your entry into the hat (bowl, whatever) from which they’ll be drawn. The person drawing out the winning paper will pull out a paper that makes good contact with their fingers. So…if you crumple your entry a bit or fold its corners in different directions, you increase your chances.
I’ve won quite a few things, such as:
$1000 in wedding prizes (discounts and freebies) in the Z-103 Wedding Giveaway (Twin Falls Idaho)
a cooler (my choice from Fred Meyer)
A lawn swing
Hostess prizes at about a fourth of the sales parties I’ve attended (I don’t like them and rarely attend)