Does it always take this many entries to actually win?

well

protip: read the forums.

You are just unlucky. Keep trying and maybe join a group.

Come over to my topic and get a chance to end your unlucky streak!

Luck of the draw.

I'm even worse off than you. I've have a higher estimated wins and the only giveaway I ever won was one that you couldn't lose, which was the Guns Of Icarus Online beta with 15,000 keys

It's just luck. You have the same chances as any user who has entered the same giveaway.

This might be obvious but if you enter a giveaway with 1249 (with you being the 1250th) entries, you have a 1/1250 chance to win, so I you try to enter many giveaways with low entries (less than 1000 for example) you will have higher chances to win).

Also to increase your chances try to:
a) create (nonbundle) giveaways
b)enter steam groups that creates giveaways only for members (like the SteamGifts.com group) c) check the forums for private giveaways.

Hope it helps :) .

There are people with many thousands, including someone with an expected win count of over 13.

Read this, it might help

I'm up to 3.12 expected wins and have gotten 0. It's just a lottery. Don't expect to win anything at all and you'll be pleasantly surprised if it ever happens.

site is rigged, staff members make people they like to win, rest have to join small groups to win lol