I'd wondering what kind of caveats I might face going sly, seeing as how I'd had hair transplants 20 years ago. I was mostly worried about scarring in the front of my scalp, from where the plugs went in.
Here's my experience, going sly, for anyone in the same boat as I and wondering the same:
The scarring in the front is not a real problem, however, wherever I had plugs put in, those spots tend to remain dark, as the hair follicle seems just below the skin and cant' be reached via the razor. In time, as my skin adjusts, maybe I'll get closer, I'm just not sure. I've used an electric razor for as long as I can remember, so I forget how that whole thing works. It's not really awful though. Just not as seamless as I would've preferred. Scar-wise, however, not a problem.
The real scars are the ones in the back - I have 3 of them, about 6 inches long, pretty deep, and one runs up towards above my right ear.
I look like I was in a knife fight, people will think I'm sort of gangsta badass! lol Not really the look I was going for, but hey, they're in the back at least. Not so bad. At least I have a story I can tell.. or make up, depending on who I wanna impress ..

So, I shall see how things develop as:
A) My skin/scalp adjusts to being shaved
B) Exposure to sun and elements "weather" my scalp, and it tans some
Hopefully, things will "even" out more. Time will also help, and probably has somewhat already.
I know I also have options such as microdermabrasion and laser treatment as well, something I wanted to do for my face anyway.. it's just a matter of $$.
All in all though, it's not that bad.
From the front, anyway, things look decent. Certainly not bad enough to prevent anyone whose had transplants in the past from going sly. If you really want to do it, just do it. You won't look anymore like Frankenstein than you probably already do, really. (Sorry, but that's how I felt about myself)


I'll gladly answer any questions anyone has, just let 'em rip.
If you want some shots of the back, I can do that too.