WOW! Lots of interesting dialogue on this topic. A big thanks to both pugdog and Eliot!

Regarding payment - a decision on payment gateways has not yet been made however, leaning very much toward the Authorize.net payment gateway. The gateway is able to have scripts provide the gateway authorizations and can deliver back whatever codes are defined in the thru/via the gateway ... user can input the code/routing.

File upload would be a definite - common file formats, Word Docs for example. Pugdog, I'm not so sure on uploading the file into the SQL table, it would seem much easier for maintenance, troubleshooting, any sort of manual intervention to have the files actually uploaded to the server and use the script to call the file.

The Job Seeker would complete a form that would include locale, keywords, etc so having the actual [uploaded] document searchable wouldn't be a key element.

Now the tough part ... availability to do the project, estimated cost for the functionality, and timeframe to complete the modifications. Thanks!