All these systems for raising and lowering the mast of a 25 footer are nice but probably impractical for your situation.
I have to respectfully disagree with you on that. I think that it's far better to have a plan to go by and stick to that plan. I'm not saying that you shouldn't raise it by hand over the bow with a few guys. I've helped to raise/lower masts from the stern on O'Day 25s and we were very successful but if there is an easier fool proof way to do it without risking damage to the mast, chainplates, or the tabernacle, one should try to seek it out and use it.
I've watched Ray and his brother in-law get the mast up on his O'Day 26 a few times without any problems whatsoever and he has a roller furler on his mast which makes the task all that more difficult.
Through the years I learned two mayor things about mast raising/lowering that can save Jack, or anyone else a lot of grief.
The first thing is to get the boat level. If the boat is leaning to one side, the mast will go over. The other important thing is the direction of the wind. If you're raising/lowering over the stern, you want the wind coming directly from the stern and vise versa. If the boat has a furler, someone needs to hold it and guide it with the mast.
Myself, I prefer to raise my mast from the stern and I do this about twice a year. My mast has a CDI Roller Furler connected to it and I can get it up or down by myself. It's 27' long and weighs about 65 lbs.
Maybe I'm wrong, but I'd rather be safe than sorry. I'd rather be able to do it myself rather than have to depend on someone else but that's the way I've always been.
Here's some pics of Rays boat and also my O'Day 222 in the mast raising process.