On any boat trip of any length things will break down. In fact, cruising has been called boat repair in exotic locations. Our little cruise had its own breakdowns.
Somehow the connector on the main antenna cable went missing. I've no idea where that went. Since I was using the handheld marine 99% of the time that wasn't a big problem. It did leave us with only one radio.
The Snow Leopard case for the iphone was a great idea. It's a waterproof case with additional battery power and a solar panel. I loved it, but it did not survive the trip. First the special duel lock on the case broke. I was able to keep it closed with a small piece of twisted wire. Then the waterproof USB door broke off. At the end of the trip, the USB port itself broke. It's too bad the case did not hold up, but to be fair, the phone would have been destroyed at least 4 times had it not been in the case.
The hand throttle for the outboard came apart and key parts disappeared into Florida Bay. While I did get it running, after a fashion, it's time to replace the outboard. A quick search on-line for the parts has been an eye opener. I've been unable to find all the parts needed, and the ones I have found are darn pricey.
One of the turnbuckles for the rigging got bent. That was my fault. While trying to a avoid the random movements of a barge I hit a dock a bit hard. In spite of being damaged it worked fine for the rest of the trip, but no need to push my luck.
There were lots of little repair jobs that were successfully completed. Upgrades to the electrical system worked just fine. We spent up to 5 days at anchor without depleting the battery too badly. A rudder control line was replaced with a heavier duty piece of cordage that worked much smoother. The new coat of bottom paint held up fairly well. Assorted pins and clips got replaced as needed.
The big Sea Eagle 420 inflatable kayak worked out well. It took a lot of abuse and still looks good. By allowing us to anchor out instead of paying for marinas, the kayak paid for itself. The kayak paddles had some minor issues. Two of the little pins that hold the blades flew off and became gifts to Lord Neptune. Oh well, so it goes. A little electrical tape held things in place. Maybe I should have upgraded to the fancy carbon fiber blades. Then again, I could build good paddles for a lot less.
The MSR Whisperlite stove eventually plugged up. Considering I was burning marine gas in it at the time, that's no surprise. I had back up parts so just replaced the burner until I get around to cleaning up the fouled parts.
No doubt there are some other repairs I just can't remember.
One good thing about being a very simple boat, there are whole systems that I didn't have to fix because we never had them in the first place. Simplicity has it's perks.