Took the collective advice and cut down the ears and the excess length of the bolts to hopefully prevent hang-ups. Thanks to everyone.
I'm a little concerned about the "wet noodle" effect of the furled jib. I'm planning to attach the main sheet to the forestay and have my wife assist with the lowering by keeping some tension on that while I manhandle the mast.
As far as baby stays: I hadn't planned to use them, unless that seems like a big mistake.
I don't think you'll have too much problem at all - as with that method you describe, the wet noodle will be drawn tight, and held in tension by the main sheet - or whatever block and tackle you connect to the bottom of it. If you use a mast raising method that does not inherently draw the mast up and down by tension on the forestay - that's more where you can run into the floppy problems.
I use a different method, with a winch temporarily attached to the mast, and a shock-cord "rubber band" keeping tension on the forestay. It sounds more complicated than it is, and both methods have their advantages. The biggest thing to watch out for is shrouds catching on some protrusion during the process - but if that happens, just back the mast down a little bit, and have someone (or yourself) un-hang it, and then go back up.
Also watch out for the bottom turnbuckles on the shrouds, and make sure they do not become twisted cock-eyed (for lack of a better term) in relation to the chain plates - there is a tendency to bend the bottom "T" bolt, if they are not angling up correctly in the "U" that they lock into. Again, it sounds a little more complicated than it is. If you cut a 5-6" piece of about 10 gauge copper insulated wire, and bend a little "hand hold" on one end, you can temporarily wedge the other straight end under the "T" bolt, between it and the "U," and it will keep the "T" bolt from getting cock-eyed in the "U" when raising the mast.
If possible, try to park the trailer so there is not a strong cross-wind on the mast. Stingy Sailor's video does a good job showing how it should go, and it's easier every time you do it. Just plan everything out ahead, and it will go smoothly.
Also, you generally won't need to manhandle it too much at all, as the mainsheet multiplier effect will do the work lifting & lowering - you just have to watch so the mast does not want to go sideways, or that any shrouds hang up - that's all it is. If the mast wants to go sideways, usually it is because a shroud is hanging up on one side or another.