I’m unsure about the pupillage award draw down but I can provide some advice about work experience / CV topping up whilst working as I’ve been in the same position.
I have taken part in virtual / online sessions to build my experience. Advocacy opportunities with the Inn are very often online, as is the advocacy club (a small fee to attend) but an evening session once a month to gain advocacy experience is good. Also I believe the FRU training is also online.
I know some Inns have paid work experience awards / prizes. I know for eg. Middle Temple has a scheme where you can be awarded a mini and marshaling and receive a payment for the expenses of attending.
Other things I have done is attend evening webinars / workshops mostly being virtual.
In terms of in person work experience such as minis & marshalling - I’ve used annual leave to accommodate these experiences. Also, looking for assessed minis can be helpful as if you meet the criteria there is sometimes a financial award for attending.
Also looking for a work from home / hybrid role can help as you’re already home and available to log in for evening virtual sessions / webinars / events / qualifying sessions etc.
I hope some of these suggestions help and good luck building up your CV! 😊