Wood Mast Sleeving question

[Idon84]

I've been talking with several people on what, if anything, I should do to the attachment points for through bolted hardware on my wooden mast. Just about all of them said I should "sleeve" the holes with stainless tubing. The holes for all the attachments are 1/2" and 3/8". See picture:

Here is the upper spreader attachment, all of the attachments wrap 3/4 around the mast like the picture:

And the gooseneck where the wood is slightly crushed already:

Over all the mast is in fine shape. The holes in the mast are not soft or have any rot issues. Notice though they have already been filled once.

My questions:
1. Sleeving prudent? Or something not to worry about? The areas where there are holes is solid wood.
2. If I were to sleeve, how do I drill a straight hole through 5" of mast so that they properly line up with the attachments? My drill press won't fit around the mast and isn't big enough for the job. (The mast is 38' long and requires multiple people to just budge it so it isn't easily moveable)
3. 1/2" hole is going to require a larger hole if I want to sleeve. Are there any drill bits, big enough 3/4"+ (not forstner), and long enough to do this? Am I missing something?

Thanks all as always.

[Quetzalsailor]

Is the mast solid at the bolts? (Is it hollow elsewhere?) I'd want to be sure no more water got into those places that are stained dark; presumably new finish would take care of it. I see a stain leading upwards from one bolt; is that a crack that's crying out for some epoxy? What's the filler at the various holes? If epoxy well bonded, I think I'd be content. At that crushed spot, I think I'd just refinish and over tighten no more. You could rout out a strip extending beyond the crush and epoxy a Dutchman into it if you think the crush won't hold a finish.

I think I'd be content to refinish the mast and bed the fittings in whatever Hirilonde likes best.

I've had to put large Dutchmen into my Flying Dutchman mast at the hounds. It's hollow and the bearing for the hounds bolt is only the 3/8" or so wall thickness of the mast. Not only were the holes hogged downwards but there were compression failure cracks.

Thin sleeves would not hurt, but why bother? But, if they were thin they would not take compression from the bolts, if thick they'd be taking area out of the mast. They'd have to be well-bedded.

[Hirilondë]

If you were attaching a bale or something similar that would swivel or move in any similar way then a sleeve would allow you to snug the fasteners and provide a bushing to keep from wearing the wood and then allow water to get in. If you had a hollow mast that would not stand up to the compression then the sleeve would become the compression resistor. But if your hardware requires a tight fit to keep it from moving and thus maintain an integral bedding, and the section is solid or at least strong enough to handle the compression of the fastener, then I would not add a sleeve. This seems to be the case here.

I would just give the spar some good coats of varnish and reinstall the hardware with a good bedding like Quetzalsailor has suggested. I like Dolfinite for wooden spars, but a polysulfide would work fine as well.

[Idon84]

Great. I was hoping to hear that. The mast is solid where the bolts go through but other areas are hollow. The dark spots you see look WAY worse in the photos than they are on the actual mast. I did double check them last night with a sharp point but the wood is still in fine condition. Agree tho that I will touch up some of those areas with a little epoxy and then coat the whole thing with varnish.

Some of the black you see around the holes is from the old bedding compound that I have not cleaned up yet.

The crushed area is VERY minor and I don't see any need to do much else than re attach the fitting and bed heavily.

Moving forward,

Thanks again!