From my limited experience, skiffs are a necessary evil. I had plans of inflating/deflating mine when I needed it (about every 6 weeks). Those plans were changed the first time I put the dinghy together. I'm on a 36' boat and couldn't imagine inflating my 10' on board. It has yet to be deflated and I doubt I will. I store mine up on the bow when sailing but would tow it if I had to.
My advice is to at least consider that what every you buy, may end up being towed. If at all possible, do you have any friends with an inflatable? See if you can borrow theirs and mess with it on board before investing in an inflatable.