Sorry to hear (read) that you're having so many problems with the tabernacle. It's truly the "Achilles Heel" of our wonderful boats, if that one part isn't working right, you're dead in the water. So you've asked for ideas and suggestions, here's off the top of my head:
-How are you cutting the aluminum mast? I'll assume a cutting disk on an angle grinder. Build yourself a jig (2x4 wood is fine) to keep everything aligned. Put the two pieces of mast side-by-side, making sure they are absolutely parallel, then cut, ideally with some mechanism to make sure you keep the blade at 90 degrees. Something like this:
https://youtu.be/_e7HDp9AMP8?t=747 and here's how to make it:
https://youtu.be/_e7HDp9AMP8?t=680By the way, that is (IMHO) an excellent woodworking channel. Japanese guy full of brilliant ideas.
-Get a "Center Punch" to start your screw holes, they've very cheap and save you from drifting drill bits. If you are uncertain of our ability to drill at 90 degrees, there are all sorts of tricks to help you out. Personally, use and old CD as a drill guide (you can check you angle via the reflection), but do some googling to see what method works best for you.
-Make sure your screw hole is the size of the INNER diameter of your screws (bottom of the threads), not the total diameter. You can easily tap the hole with a Harbor Freight tap and die kit. But if you use stainless steel screws (and you should!) then it will self-tap, i.e. cut it's own grooves into the aluminum mast. Go slowly, carefully, and use some tapping oil (lubricant).
-Do you really have to cut an entire 0.75 inch on both sides? If you're only off by a few mm? Or is this because of your bad screw holes? I'd almost be tempted to redrill and then tap a larger hole into your tabernacle plug, but you'll need a drill press for that....
-Are you in Raleigh, NC? (From your onscreen handle)? If so, I'm in Durham, near downtown and lucky you, I have a spare, broken mast. You're welcome to come by, cut off a length of my mast and use it as the bottom part of your rig (base of the mast, from keelson to tabernacle). Likewise, I have a spare two-pin tabernacle floating around in my "junk drawer," you're welcome to it. I also have a fairly OK drill press, and we can see if the mast plugs from my old mast will help you. Also have a compound miter saw, so if you can source a metal cut-off blade for a chop saw (Dewalt makes one), that solves your 90-degree cutting problem. Anyway, if you're nearby and willing to run over to Durham - bring your entire mast or boat if you want - I'm happy to help out. Private message me.