I'm confused. Do you want to use the $200 to pay people, charities, or a dating fund when you derail? Beeminder does not allow that directly, but you are free to do additional things when you derail if you want. However, Beeminder does have "supporters", who will get an email when you derail, and you could use this to do something similar (like get them to bug you to pay them).
Yes, either, and, or.
If it's worth saying, but not worth its own post (even in Discussion), then it goes here.
Notes for future OT posters:
1. Please add the 'open_thread' tag.
2. Check if there is an active Open Thread before posting a new one. (Immediately before; refresh the list-of-threads page before posting.)
3. Open Threads should be posted in Discussion, and not Main.
4. Open Threads should start on Monday, and end on Sunday.