Keep in mind that carry on regulations wary between airlines. While say, AA and Delta are quite generous, Fiji Air and Virgin Australia will allow only a 15 pd piece as carry-on. Allegiant sets limit for both check in and carry on at 40 pd. They'll let you in with a 50-pounder but you'll have to pay extra $50. Etc, etc...
That's a very good point, make sure that you know the baggage allowance and carry-on policy for your airline. One time in the Bahamas we were flying a small plane to an Out Island and they weighed both the passengers and the luggage before deciding what could travel on the plane with us.
Years ago, when traveling in Central America (Honduras or Belize, I think?) we had to select 1 checked bag - for both of us - that they labeled special and guaranteed would be put on the plane with us.
When we travel to the Cayman Sister Islands on a Cayman Airways Twin Otter, you are allowed a total of 55 lbs luggage per person and that means everything, including carry-ons, and you may be charged per pound for overweight baggage. You won't be allowed any large carry-ons (no rollerboards or large back packs, etc.) because large carry-ons will be placed in the baggage hold.
It is not unusual to have a bag delayed by a day. This is a bigger problem for Little Cayman because Cayman Brac has a larger airport that can accept bigger planes and jets both day and night. The small airport on Little Cayman can only take small propeller planes and only during daylight.
The last time we were there in 2017 the suitcase with most of our clothes was delayed for a day. Another couple had the bag with all their dive gear delayed - but the dive shop loaned them gear for free until their stuff arrived. I tend to bring a large purse that I can jam under the tiny seat in front of me and I pack it with essentials like medications, glasses and contact lenses, C-cards, swimsuits, and clean undies, phones and dive computers, just things that we will really need if our luggage is delayed. The staff at the LCBR laundered our clothes for free to help us get by until our missing bag arrived.
We've had bags delayed elsewhere, Cozumel and Bonaire and other places, but they usually show up within a day. It is inconvenient but it usually works out.
The only damage was when we made the mistake of bringing a bottle of Tia Maria back from Mexico in our checked baggage. We thought that we had padded and protected it well but it broke during transport. The bag was leaking and we could smell it on the conveyer belt at the airport; most of the stuff inside was ruined and so was the suitcase!
The weight difference is negligible. You will replace your standard roll aboard multiple times and you will not with this. I see no advantage to going the standard roll aboard route. AND, there are times when they will MAKE you check your carryon whether you want to or not. To each his own!!!
