- Yes the site is still maintained / up to date. A couple of the more recent jobs have been taken up if your wondering why its only older postings.
- Yes of course you can post here.
As for organizing payments it will depend on the freelancer you contract. PayPal is quite a common form of payment (usually on smaller gigs). Some freelancers will require a deposit or small up front payment as well. If your looking for developers you can also look through the developer network http://www.silverstripe.org/silverstripe-developer-network/