I have a sound hole pickup in my acoustic and am sick of the dinky wire going to my amp/DI box. I have some 1/4" jacks with reinforcing plates, I used one to replace the non-plate jack on my bass, which was always wobbly. I was just going to drill a hole and install one of these plate jacks in the location you see it in most electric guitars, but in reading it seems most acoustic players opt for the endpin jack, and some have said the side wood in the guitar is too thin and can be damaged by a jack there.
1. I've seen acoustic guitars with side pickups which seemed to work fine
2. I've always found endpin jacks clumsy and annoying for some reason
3. I already have the regular jacks, and they have the reinforcing plate, which might help the strength (?)
4. I don't want to break my guitar in spite if the above 3 statements.
Anybody have experience or advice in this area (or a redirect if this is an inappropriate question for this subforum)
A guitar is a kind of bellows driven by vibrations in the top. It's the most important part of the instrument.
In a good guitar, the top wood is carefully selected from (usually) the stiffest and lightest spruce a luthier can beg steal or borrow. It's thicknessed very precisely and then braced to a very specific pattern with hand-carved braces. Throughout the process the luthier will be tapping away and listening to how the wood rings out, shaving and sanding at each step to tune in the desired sonic qualities. The weight of the top is crucial: it has to be as light as possible without actually falling apart (hence the need for stiff types of wood). Bridge pieces are weighed out to the gram. Even the weight of the finish is taken into consideration.
So no: you don't want to bolt a jack socket on to the top. It'll affect the structural integrity and the mass will stop the top vibrating in the way it was designed to.
If you ever plan to work on any kind of wood acoustic instrument, you must ask a luthier for advice. They're not just shipping crates with strings.