The typical in-mast mast-step base will be about 6" high for your boat. There should be a pin through it (keeps the mast from jumping off the deck in a rollover). You
will have to lift the mast-- it won't just tilt over or slide off. There's a reason why not.
When I took down my rig, the mast was 'welded' to the SS 'tabernacle' plate with bimetallic corrosion. I had two 11th-grade football-player students helping me and we were literally leaning on it to knock it down (with three loose 'safety' shrouds still attached) and it wasn't moving. It was the very devil. My new mast step is
not a tabernacle (who lowers the mast to trailer/daysail a H25?) but a proper fabricated-aluminum mast-step base which I designed and had made (and can sell a copy of

). So I have to lift my mast off and lower it on, just like big-boat owners do!
The short answer you're probably looking for is: I'd rely on the crane for this.
In my (not inconsiderable) experience, this job can be either the biggest anxiety or a walk in the park. So forgive me if this sounds like I'm talking down at you. First, remember that as you loosen (as with tuning) one rigging wire, you need to turn its correspondent at the same time. Alternating with a few turns at a time on each is acceptable. What's
not acceptable is spinning the turnbuckle way open on, say, an upper shroud without ever touching the other one. Having some amateur or on-staff mooyock 'helping' by doing this 'for you', or, worse, loosening and removing them all at once, causes havoc and headaches you can't begin to imagine. As our dear late Fred Thompson says in
Red October, 'The Russians don't take a dump without a plan, son.' So it should be with a chore like this. Know what you're doing before you do it, then just follow the system.
Before the crane comes, take all the rigging wires off
except either the forestay, if you don't have a furler, plus the two aft lowers (as I prefer) or else the four lowers. People with H37s and other double-headsail boats should choose the inner forestay and two lowers (running backs instead of standing lowers are even better). When rigging or derigging, these are the most preferable to put on first and to take off first. You can set the rake and adjust the furler before even hooking anything else on. Best of all, you can dismiss the expensive crane guy earlier. Derigging the boat is the reverse-- leaving just these three or four on, you can do more work before he arrives and starts charging you.
If the furler promises to be a nightmare, lead two (
not merely one) jib halyards forward to the rail beside the stemhead, take up on them well, and then loosen the furler. It's best to get that thing detached from the stemhead, to wrap the drum in bubble-wrap or carpet, and to draw it all the way back to the chainplates,
outside the boat, against the hull, with maybe a line or two around it, kind of high up (try lasso-ing the spreaders), tying it
only to the mast. Every rigger and crane driver hates dealing with the furler. Keeping it tied close to the mast will keep it from having its way with gravity and all that; but it will still be a problem-- that's guaranteed.
Do the same with all the rigging wires you took off, all the halyard tails, and all the flag halyards (which are often overlooked). If you can reach and detach the lower parts of a split backstay (and the whole adjuster), that's a no-brainer. The wire and especially the turnbuckles will be very adept at dining and scratching everything they can. You can pad them or try to catch them; but it's part of the price of the chore. On Diana I can spin the TB bottles off at the upper ends and leave them on deck (till later), so they're not on the wires when the boat is being rigged or derigged. (This is a surprisingly elegant solution to a bit of a screw-up; it's in my blog.)
As you do this you'll discover why all rigging turnbuckles have more threads inside the bottle at one end than at the other. On my boat the longer threads are at the bottom.
Collect all the clevis pins and over the winter inspect them for corrosion. Throw away all the cotter pins-- reusing them is the very definition of false economy. Do not rig the boat again using roll pins. Roll pins break and find their way off the job. The rig needs for the cotter pins to be bent at the proper 15-degree angle (or better). The classy way to treat these is with white rigging tape, not great blobs of silicone.
The crane guy will know how to sling a harness round your mast to lift it. Almost always it will be under the spreaders, which is not high enough. The furler (and anything at the top) will tug on the top of the mast and try to tip it; so have a guy stationed with a tether line secured to a point very low on the mast (halyard winch or cleat, at the
highest) and be able to drop this line to another person on the ground when the mast moves off. If it's windy, station two guys on this line-- they will have a fight of it. Like the spotter in a MOB rescue, these guys should do
nothing else till the mast is lying on the horses on the ground. This task tends to be the most underestimated of the whole chore.
Speaking of horses, I hope you already have yours made. I have three, with little plywood fiddles screwed standing-up to the side of the horizontal part (this is why folding and metal ones are no good) to hold the spars. Two have three U-shaped cutouts, for the boom, the spinnaker pole and the mast. One has only one, for the masthead. You can line the U-shaped cutouts with carpet if you're worried. Be sure all the horses' legs are well-braced and gusseted. They take more of a beating that you might imagine. If they're too pretty they can also walk away. Station them near where the boat will be, or where you are expected to work on them, before the crane guy shows up. Be sure there's a clear space for him to lay the mast down. The cheapest way is to have your own crew move the mast. My mast (30') weighs 66 lbs. With the rigging it's more; but three guys can move a H30 mast, fully rigged, with no damage to backs.
Take all your shackles, clevis pins, antennae, wind-instrument senders, and detachable halyard blocks home for the winter, or they may not be there next season.
The more of this you can have ready before the crane arrives, the better. In our area the crane is $400/hour, one hour minimum. This job will take him about 20 minutes. See who else in the yard needs a crane and schedule one crane visit and split the fee. You'll be glad to make and keep such friends!
