Has anybody ever installed a strap peg (front) on an acoustic guitar? Seems pretty straightforward but I don’t want to mess my guitar up. Any words of wisdom or caution before I proceed?
Tying the front of the strap around the neck looks cool if you’re Johnny Cash but it kind of gets in my way. 
I’m think it’d work perfectly on the heel of the neck, underside. Am I making a mistake by not letting a pro do this?
I did it myself on both my acoustic and my tele. Don’t worry, it’s a fairly simple procedure.
Drill a pilot hole on back of the heel of the neck where you’re going to attach your strap button. Make the hole just a little bit smaller than the screw. It needs to be big enough to prevent the wood splitting, but small enough for the screw to have something to grab a hold of, so use the biggest drill bit you have that’s smaller than the screw. Drill slightly deeper than the length of the screw.
Then you just screw on the strap button. You should have no problems as long as you drill the pilot hole.
If you’re unsure about how big to make your pilot hole, http://www.naturalhandyman.com/iip/inffastener/infwoodscrewpilot.html has a chart telling you the reccomended sizes for pilot holes for each size of screw. You’ll be drilling into hardwood. The chart might help you if you’re really unsure, but honestly, I have bad DIY skills and I did just fine by eyeballing it. So don’t worry about it. 
Hope this all helps.
I installed one on my D18 about 6 months ago. Like you, I was kind of worried about it, but I did some research and got some advice here, and it installed perfectly for me. I looked for the thread I started here, but I guess it was over on the old site.
Before I drilled, I found Martin’s schematic on the recommended button location and followed it. I also taped the heel and used a depth guide on the drill bit. I ordered the little felt washer along with the button and I think that was a good idea. It allowed me to snug up the button without digging into the wood.
You might want to make sure the button won’t be in your way if you have a cutaway or play up the neck a lot. Also, make sure the guitar will fit in your case once the button is installed. My heel button made a new indentation in my case, but didn’t stop me from using it.
Good luck!
Thanks for the input fellas…I think I’ll give it a shot.
Use a drop of dish soap or polish for lubrication. It’ll also swell the wood ever so slightly for a very secure fit. If your guitar happens to have a bolt through the heel into the neck block(you’d be surprised), be sure to miss it.
Steve