Hello and Welcome Dawgneck!
I was in your same situation since I started shaving as a teen. I have literally tried everything to get rid of my razor bump / ingrown hair problems. I used a product called Tend Skin religiously for years and it worked pretty well at preventing bumps and ingrown hairs. The problem was it excessively dried out my skin, it stunk, made my skin look not-so-great, and it was expensive. I tried Bump Fighter razors, which worked OK, but didn't shave as close as I wanted and also didn't entirely prevent razor bumps. And of course, I've tried just about every Foil/Rotary electric shaver/trimmer known to man. None worked well for me.
I started using Extra Virgin Olive Oil to shave my face with a few weeks ago, and it has been the only thing that completely eliminated the problem for me. I could even shave with a Mach3 and Olive Oil if I wanted, but the DE offers a much better overall shave and makes my skin look and feel much better (especially the day after the shave). I also now only use Cetaphil to wash my face afterwards and apply a light moisturizer. (I think the key may be to keep the skin hydrated and soft so the hairs don't get trapped under the skin.)
I'll leave it to the seasoned pros to offer you tips on gear, technique, etc. but definitely try shaving with Olive Oil (just rinse with hot water first, apply and reapply a hot towel for a few minutes to soften the stubble a bit, apply a generous amount of oil, and shave).
Cheers,
Jon
Merkur Futur, Dovo 5/8, Silver Steel 6/8 (Unknown)
Rooney 1/2 Super Silvertip
"It's all about bucks kid, and the rest is just conversation."
Jon
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