I've seen a lot of boats on moorings with the headsails shredded. I would say, though, that if it is the mild
weather season of the year, you'll probably get away with it for just 3 weeks. Three months, now, i'd say just bite the bullet and take it down, unless you WANT to buy a new sail now.
If the
dinghy is easy to put below, or if there is a safe place to leave it ashore, those are preferable. That said, we have left our
RIB (which won't fit below--too wide for the companionway) chained on
deck, disinflated, and upside down. How we carry it on passages.
Sailboats are hard to lock effectively (unless made of metal, and with an eye to
security from theft), so anything desirable will always be somewhat at risk when you are not on the boat. My husband, Jim, says it's like locking a tissue box. So, I think your dinghy may be safe below on the boat, and still, if it is brand new and you paid top dollar for you, then safer (however you figure out to do that) might lead to more peace of mind.
The
bimini can usually be reefed, and I wouldn't worry about leaving it like that.
Now, if early season cyclone ends can get to it at your location, then, of course, prepare the boat for a
hurricane, and next time, if you take notes and learn from the first, it will take less time and be even more thorough.. Unfortunately, big weather systems are totally careless of what we boaties want.
It is kind of your friend to come aboard after weather
events to check the boat, but do not count on him to fix stuff that isn't right on arrival. Also, double up on your
mooring lines, so that if there is chafe, there are backups in place: you won't want the boat to go walkabout.
One other note, if you are going to leave the
bilge pump on, be sure that the through
hull is open so the
water can get out. Even just a thunder
shower can drop a lot of rain, and coming back to a fetid sump isn't fun.
Ann