To get your XP and clear it from your chalkboard the following tasks must be done after they appear on your chalkboard:
1) buy record player from Ian (the record player sits ON the table)
2) buy the record box from Ryan (the record box sits UNDER the table)
3) buy a record from the shop
4) play a record.
Be sure to do all of these tasks only *after* they appear on your chalkboard. If you do them before the task is on your chalkboard, the task will become stuck on the chalkboard.