The Fishman switchjack will fit through the F-hole. It is a modified (threaded) Switchcraft. I have literally installed hundreds of these. There are some mandolins it will not fit in, never had a problem with The Loar. You have to twist it around and carefully get it through.
I am in agreement on that Mighty Mite jack there. These are not the greatest quality and the cable fit is a bit sloppy. The best quality is the Fishman, but there is also one from Italy that is great quality, but not readily available. LR Baggs uses them.
Careful of the cheapies you can get. There are some that look nice, but again, sloppy cable fit and softer metal that doesn't standup well to the cable stress.
The step drill works great for drilling through the side of a mandolin, but not for the end pin. There isn't enough depth.
I use this:
http://www.stewmac.com/Luthier_Tools...ck_Reamer.html
Maybe not realistic for doing only a couple of installs, but you just can't beat it. It has reamed countless holes and is still going strong.
If I were just doing one install, I would use a standard bit, drill part of the way through with a power drill, then finish by hand. In fact, I do have to occasionally do this on mandolins where the reamer will hit braces (flat tops).
Somewhere around 1/8" to go, is where the bits catch and tear through, causing cracks. If you have drilled through un-backed wood, you have most likely experienced this. Tailblocks are especially prone.
Lastely, you have two options of how you mount these.
You can drill through the tailpiece with it on the mandolin. This is quick to drill, and you have perfect alignment of the hole with the tailpiece for a good endpin fit. Downside, you will have to adjust the thread depth by test fitting the jack a few times (from inside the mandolin).
This route, I insert it from the outside visually check the depth by looking through the F hole, make the basic adjustment, then test fully installed and pull it out and do the final adjustment.
Second option is remove the tailpiece , drill the hole just a little oversized and then there is no real thread adjustment needed. Downside, is potential alignment issues. This doesn't work with cast tailpieces as they are too thick.
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