Yes, you can enable our system to request a player's handicap by going to Manage Event and select Event Settings. On this page, you can turn on/off the option to "Ask for Handicap".
If you would like to ask a custom question, these need to be setup in Manage Event -> Registration Packages. You would to setup these questions by clicking on a specific registration package.
If you ask the question of the registrant, it will only be asked one time.
If you ask the question of the golfers, the question will appear for each golfer included in the package. For instance, if it is a foursome package the question would appear four times.