A nice feature back in the day of VB6 was being able to set a break condition. Essentially you could create an expression along the lines of "Break when variable X = 'my value'" - would be a nice feature and removes having to create IF actions with a breakpoint...
That is something I would like to see… but it will need a redesign of the internals. Watches are not connected to the debugger at the moment, they just listen for messages the core sends when variables change values. I’ve been spending some time lately thinking about some internal changes to the way debugging happens, so it might just happen for the next major version (no promises though).