I'm not sure where the talk of grounding came from. That's about the only mistake I DIDN'T make- I never touched the bottom.
I was using my smaller jib. I think the dang boat came with a 110 and a 130. I'd really like my "working" jib to be a 90 or 100.
The jibs appear to be in pretty decent shape, it's just the main that's "tired but serviceable". I've already priced a replacement so I'll buy it come the Spring.
Riddle me this folks:
If I'm supposed to prep the jib before I get underway, how do I keep it doused, and under control while I motor out to the area where I have enough room to raise sails? Do I just pile it up and place something heavy on it or what?
I'm old-school, no roller-furling system.
As you know, I'm not real keen on having you out learning how to sail in the middle of winter, especially with kids aboard. But if you're going to be out there anyway...
Don't worry about that smaller sail being a 110 instead of a 90-100. A 110 is actually a pretty good size to have on Chesapeake Bay (I wish I had one!) along with the larger 130 +/- genoa. With a reef or two in your mainsail, you will be able to handle the vast majority of conditions that you'll encounter on the Bay. So don't feel disappointed about that, it's a good sail to have.
As for prepping the jib before heading out -- good plan. We have roller furler on our current boat, but I've sailed thousands of miles on boats with hank-on jibs. Our normal routine was to hank the luff of the jib to the headstay with it still in the bag, secure the tack and and attach the halyard at the head.
Depending on the sail bag and how well it secures closed, often nothing more is necessary than to tighten the bag cinch. Sometimes, it's helpful or necessary (for instance, when the sailbag can't be left on) to secure the head of the sail with a gasket (i.e. sail tie), by running the gasket through the head cringle and down to the stem fitting where the tack is secured. When it's time to hoist sail, someone goes forward and removes the bag and/or the gasket.
I have seen, but never used myself, an arrangement where a downhaul is used with the headsail, that can be manipulated from the cockpit. This might be a good arrangement if you expect to be shorthanded most of the time.