Separate hole in my opinion. The tailpiece only has a hole big enough for a screw. You do not want to enlarge it.

Separate hole in the tail block. (NOT THE SIDE)

There's no other option if you have a guitar with a strap lock.

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Originally posted by hlpdobro

Separate hole in the tail block. (NOT THE SIDE)

There's no other option if you have a guitar with a strap lock.

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Good advice on the location. The K&K PURE RESONATOR SB pickup installation instructions actually show it installed on the side but that is a thin and therefore weak point on the guitar. Too bad I drilled a hole into the side of my Regal before I was advised not to do that (here). All is well now - the Regal belongs to someone else.

I recall in the early years when National was making the Scheerhorn aka "Nati-horn" guitars, which have been in regular production for ballpark 12-13 years, they were mounting the output jack on the treble side lower bout, about where you typically find a jack on a solid body electric guitar.

I've seen this in the past on a few other resos, but they seemed to be on  inexpensive instruments.

Frederick mentioned instructions from K & K with their Reso pickup, but of the examples I've heard - it doesn't sound very good to begin with. K&K has an excellent reputation for their flattop acoustic pickups, but  as we know,  amplifying a spider bridge resonator is a different beast. 

I was surprised to see these side mounted jacks  on a high level U.S. made resonator like a Nati-horn.  In order to do this, obviously there has to be some sort of reinforcement inside the guitar to mount a quarter-inch jack in that area - no way would you install it where there is just the very thin tonewood. 

No idea if National still does this on Nashville pickup factory installations, but they've marched to a different drummer over the years in some of their construction techniques.

For example, and this is also done with the Nashville pickup on relatively inexpensive Gretsch resonators like the Bobtail, National doesn't use anything like a Beard adjustable spider when doing factory installation in a Nati-horn. 

Years ago I had National Guitars install a Fishman Nashville pickup in my National Scheerhorn. I was somewhat shocked to receive it back with the output jack installed on the treble side lower bout rim. I always hated that installation spot - the 1/4” guitar cabling would occasionally throw the balance of the guitar off while standing.  (Before I had a wireless rig...).

Yeah, tail block, separate hole.

I have my own internal and external amplification set ups mounted in one of my Harlow resos aside the end block wIthout issues for quite a few years. I do my own installs quite securely, and they are quite stable i'll leave it at that. I didnt and still do not like how the straplock and strap would interfere with the other jack(s), had I placed one or both on the tailpiece block. Whether i use one or two of my wireless options,  or if i use a wire, there are no balacing issues when i use the guitar so I guess im lucky. I have options depending on the Sound man's abilities.  YMMV.