Wouldn't the side stays need to be disconnected to drop it forward? They don't if you go back
You are absolutely right.
I can only speak for the O'Day 222 and all I can tell you is that the chainplates on my boat are aft of the mast. It's impossible to lower my mast over the bow without messing with my stays. Even if I could lower my mast over the bow, the mast would be top heavy.
The distance from the tabernacle to the bow pulpit is shorter than the distance from the tabernacle to the stern rail. This also holds true with the O'Day 25 and 26 I believe.
OK. So this fellow really doesn't need to build anything elaborate to hold his mast from hitting the top of the cabin if he chooses to lower aft.
He can use two 2x4s and bolt them together like a giant pair of scissors and rope it to his stern rail. The mast can be lowered aft and will rest in the apex of this makeshift rig.
He could also secure a short step ladder to the rail for the mast to lay on.
All he needs to do is remove his boom. He can leave the sail tied to the boom and stow it in the cabin to get it out of his way.
Then loosen his forestay and remove the front pin on the tabernacle.
He can use his Jib halyard to hold the mast up by attaching the halyard shackle to the bow stem chainplate and cleating off the halyard.
The forestay can be removed and bungeed to the mast so that it doesn't flop around.
Close the sliding hatch and stand on top of it and hold the mast while his crew mate lets the halyard off and unshackles it.
Before the mast is let down, the crew mate walks aft to the cockpit, straddles the seats and is gets into position to assist in the mast lowering if need be. Nobody should be walking on that boat while the mast is being lowered.
The mast can now be let down by hand without the aid of a Mainsheet tackle.
These masts are a little cumbersome but they're not heavy. If he picks a nice quiet protected spot to anchor in, this operation will come off without a hitch.
Note: Instead of hooking the Jib halyard shackle to the bow stem chainplate he could do the following which I think is easier;
If he has a single sheave block he can attach it to the rear hole in the bow stem chainplate and run a 3/8" X 60' line through it and attach it to the Jib halyard shackle. Run the halyard all the way up and cleat it off at the bottom of the mast.
The line can be taken around the mast and
over the goose neck fitting. Pull the slack out of the line and draw it up good and tight and tie it off to the bow cleat. With the line holding the mast, he could remove the forestay and bungee it to his mast. He could also untie the line and hold on to it tight and walk to the mast and get ready for his crew mate to get into position just in case he is needed.
I did this by myself for over eight years when I trailered my O'Day 222. Believe me, it's not hard. I did it so many times each week that I could do it automatically without thinking about it.
I wouldn't attempt it with a roller furler connected to the mast though. This is where a Gin Pole really comes in handy.
If he has to motor any great distance to get to the bridge, I would advise him to unpin the mastl, bring it forward, and tie it to the bow and stern rails. All the stays can be left connected and bungeed to the mast.