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The French drain sounds like a plan to me. Good idea to use the landscape fabric to stop it silting up. If you can unblock and re-use the existing pipes at the bottom, all the better.
Heheh - it was just the best image I could find!
I'm pretty sure that's the weed known as 'fat hen'. Don't let it seed as it produces 20,000 seeds per plant - if it did come in the compost that might explain why! See here:
good general weed identification page:
Andy, if you have enough peppers growing on the plants at their current size you could leave them be but potting-on to a larger size pot will allow the plants to keep growing in size and produce more flowers (plus they will need less watering and feeding.) One thing to bear in mind is that if they happen to accidentally dry out for a short period, they are likely to drop all the flowers and may be reluctant to start folwering again.
There are too many variables (feeding, temperature, sunlight) to have any chance or giving a sensible answer to that - try not to get so hung up on dates as plants grow according to conditions, not calendars!
Pumpkins and squash will keep growing until the first frost. However, pick all the fruit and bring indoors when the first frost is forecast as they won't keep once they get even a small frosting.
It's really best to use canes as the weight of the fruit is enough to snap the stems. Mine have 3 thin canes tied at the top with a few rings of twine tied between. Their stems are quite brittle.
The usual advice is that they can't fly above 18" (45cm.)
Yes, if there is a growing tip appearing on the end of the flower truss, treat it as you would a sideshoot and pinch it off above the last flower. Certain varieties do this a lot - my black russian and brandywine do it on almost every flower truss.
Slugs/snails are almost certainly the problem. They don't alwyas leave trails, so go out at night with a torch (which is when they come out to eat) to confirm.