Mast down & up in 30 minutes. Any qualifying designs?

At the 24:00 mark, Dylan raises the mast of Katie L (Hunter Minstrel) with little effort. He is cheating a bit since he doesn't use the regular mainsail, so he doesn't have to deal with the boom and gaff.
 
If lowering the mast is to be done every trip, consider using a gunter rig, with its short mast, avoiding the hassle and weight of a full length Bermuda spar. My first boat was a Gunter rigged Lysander. Rigging the mast was a one-man job taking less than a minute. It sailed surprisingly well.
 
Lysanders provided a lot of fun. A gaffer can do the lifting bit nearly as easily, as the gaff and sail remain low until one gets the mast up. Not a lot different to gunter.
My current Oughtred boat is a gunter sloop and I carry it all set when trailing., just the forstay to secure after pushing up the mast with the heel in the keel step. Slightly slower than the cutter I mentioned above, as I then hank on the jib... Only a 15ft boat, so light gear. But my reference to the Cape Cutter 19 might be of interest to the OP. Just dépends on budget. Might be a bit of a waste on a river though. More roomy that a Shrimper and quicker.
 
An Anderson 22 owner had a mooring* at Looe so every trip meant lower the mast, get under the bridge and outside, raise mast, go sailing, then the same in reverse on return.

* Just to make it more interesting his mooring / berth was in one of those floating cradle jobs.

He simply fitted a permanent stainless A frame, which went horizintal on either side of the foredeck when the mast was up - the mast step is already on a pivot as standard.

With a bit of forethought and planning I'd think almost any boat under say 25' can have an especially easily lowered and raised mast.
 
A small cabin would be good for back to basics style cruising/camping but anything between a Drascombe Lugger and a Cornish Crabber 24 Mk1 would tick my essential boxes.

You can probably adapt just about anything small to suit. The mast on my Westerly Jouster (21') was 25'6" long and I could just about lower and raise it myself, unaided. With shrouds tied loosely to the guardrails it could be lowered with the jib halyard taking the place of the forestay ... that ran out of effect just when I could take the mast on my shoulder. Re-erection was, as the Haynes manuals say, a straightforward reversal of the removal process. If I had done it more than occasionally I could have made it slicker.

I currently have two small boats. Raising the main mast on the Drascombe Longboat is a doddle; you just push it up, hold it in place with a temporary rope behind it and secure forestay at your leisure. The be-cabined ones have tabernacles, which should make things easier. My Hunter 490 is a bit trickier, because the mast is longer and because the boat is smaller, which makes access to the foredeck while afloat harder.

Sorry, a bit rambling.
 
One thing not covered here is: How low are the bridges? Does one 'dip' the mast to say, 45° or does it need to go much lower? Like the Broads lot.
Here on the Charente, dipping to about half way would clear most bridges for our small boats.
 
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