I think that raising from the front may be tricky due to the self-tacker, but I've never tried.

I've never had to raise the mast on my own, but I have taken it down solo with no problem. The only bit I use help for when raising it is having someone hold a trapeze wire to keep it up once I've raised it.

If you tie the spin halyard to the bridle wire and then cleat it at the base (I think I used a jib cleat) it'll hold the mast up fine while you attach/detach the forestay. I always put the trailer behind the boat and rest the mast on the prop while I sort out the rigging. Starting from here, it's pretty easy to lift it whilst standing on the tramp.

Paul