Barrel jack replacement...

An electrosocket is a type of jack cup originally made as an aftermarket replacement for Telecasters which have a fiddly jack cup with an annoying retainer clip.

The electrosocket requires a 7/8" hole which is a lot bigger than the hole for your barrel jack. It is secured by two screws (same size as used on Fender pickguards). You thread a standard Switchcraft output jack into the electrosocket.



With a jack threaded in:

 

An alternative would be to enlarge the hole just enough to fit a switchcraft jack and then mount it with a jack plate similar to a Les Paul:

 

It sits right on the outside of the body.

 

I do like the extra beefy Electrosocket setup and I'm not especially fond of barrel jacks.
But when a barrel jack does go bad on me, I just replace it with a new one made by Switchcraft. I haven't had one of my replacements need replacing as of yet.
I myself would not be inclined to put a 7/8" hole in the side, unless maybe I had the whole body stripped down for refinishing.

 

One last consideration with electrosockets. Take a look at this picture of a tele body:


If you look at the section where the output jack is, you'll notice the body actually flattens out. This allows the stock jack cup to sit flat against the body. This is what the electrosocket is designed to do as well.

When you put an electrosocket on an instrument that doesn't have a flat spot on the body the electrosocket won't sit perfectly flat and flush. It's a small discrepancy that only you will notice but still...

here's a super close-up of a tele I built using a Warmoth body that doesn't have the flat spot (and yes, it bothers me enough that I am planning a convert it to a plate):

 

I put one on my Squier 50s P without a problem.

The Squier has no flat spot but the curve isn’t as tight as a small tele body.

The stock hole fit the electro socket perfectly and it’s flush with only the outer lip exposed. Keep in mind my bass used the vintage Fender type tele cup.

If you open your hole up the right amount, I think you can get it to sit nicely. Get an. Non-metric electrosocket and thread in a Switchcraft, tighten it well, and forget about it for decades.

 

There's also a "football" shaped backplate (which only makes sense if you think of American football instead of the sport the rest of the world calls football), an oval plate that's bent. Those work very well for rim mounting a standard 1/4" jack on a Fender-style Fender-style instrument. The advantage over the Les-Paul style plate is the only use two screws to hold them in place and those go in the center of the rim.

Oval Jack Plate | stewmac.com

 

One of my first mods on a Tele is the Electrosocket, it's a quality piece of kit and designed to fit on the flat part of the Tele's body and fit into the already drilled hole.

It won't fit flush on a curved body and will be noticeable, especially if you have any degree of OCD!

In your case I would use an external plate as other people have suggested. Personally I think the football plate is the more elegant solution.

Just one point to bear in mind, depending on the hole already there, it might be a tight fit to get the Switchcraft jack socket in there. But a quick bit of surgery with a Dremmel will sort that. If you need to do any surgery, either remove the electrics or srick the vacuum cleaner hose inside to collect the dust as you do. Pots and PCB's full of sawdust doesn't help ....

 

Just note that the football or the square mounting plate may or may not fit the contours of your bass without modification. I've had to bend many of them for a good flush fit when replacing barrel jacks.

 

What I like to do before drilling through the 7/8" hole is to just barely kiss the surface with a forstner bit that matches the diameter of the outer rim on the socket (I can't remember the diameter off the top of my head, it may be 15/16"). Then drill through the 7/8" hole. This way, you end up with just a tiny hint of a recess for the lip of the socket to sit in - it doesn't sit fully recessed and it's not totally proud of the surface, either. That recess isn't even cut all the way around the diameter of the socket, I really just let the drill bit make contact along the top/bottom and it basically cuts out two little crescent moon shapes instead of a full circle.

The result is that the mismatch between the body curve and the flat socket lip gets lost - you don't visually see a gap, and your eye is less able to pick up on the difference between the flat vs curve shapes since the curve gets hidden against the side edge of the lip, instead of being exposed as an obvious gap, if that makes sense.

A picture is worth a thousand words, but I'm probably only a 500-word photographer, so I hope this makes sense. I tried to get a closer photo but it just got blurry...



All that said, I would never (personally) choose to switch jack styles purely because of perceived reliability of one style over others. Yes, barrel jacks fail (regardless of brand, I've got one bass that's on it's third Switchcraft barrel jack in 20-ish years). But to me, the effort of switching styles is probably a wash against the effort of having to slap in a new jack every half a decade or so. If you're worried, keep a spare and you can swap it in about 2 minutes with a soldering iron. And "normal" jacks fail sometimes, at any rate. So, in the end, I choose jack styles based on how it fits the overall look of the instrument. The electrosockets have a nice clean look, but it also strikes me as a touch retro - while a barrel jack comes off as more modern, and fits a modern-looking bass better IMO.

Also something else regarding getting a good clean look with electrosockets:

I like to thread a nut down on the jack before threading it in to the electrosocket. Then you can adjust the position of that nut to act as a "stop" for setting the depth that the socket threads onto the jack, which lets you control how far the jack sticks out past the front of the socket. I don't like to leave a lot of the jack sticking out, as is shown in this photo - I think it looks cleaner to keep maybe only half a thread sticking out versus having several threads past the front surface of the socket as shown here.

 

I like this look too. The downside being that most right angle plugs won't reach unless you have the jack protruding as far as it can.