Inflate/deflate with each use sounds like a total butt pain to me. I use an 8' Achilles on my Catalina 309. I don't need it for daysailing. For weekend and week+ trips I bring it along. Usually tow it.
It has a roll-up wood floor and yes, I can inflate on the bow or the cockpit. Would NOT go through that for each use.
Let me ask you this: do you want to pull it out of the water, roll it up, and put it away wet? I've never put mine away wet, and wonder what input others may have on this regards mildew, plague????
We also use Kayaks on some trips. I lash them to the bow. Not a bad way to go, but without a swim platform, they could be tough to deal with. Can't take a passenger (other than our cats), but they'll haul a fair amount of gear. Don't like to tow them, but they're fun to play with once you get where you're going.
The perfect tender does not exist. They get you around, but they also make you work...they seem to kind of own you.
All that said, an inflatable IMO is likely your best bet for what you're doing.