Let me clarify what I meant by wilderness "rogue". I did not just mean having wilderness skills. Of course they have always had those.
What I primarily meant was being closer in class function/role to a fragile "striker" rogue than to a "sturdy warrior". Secondarily, I include having lots of non-magical skills versus primarily shining as a warrior.
It's not a wilderness rogue you are looking at, but the term skirmisher.
I think the lightly armored started with 2e with the entire stealth and two weapon fighting requirements. That put an idea that the Rangers would not be as heavily armored as a fighter, but they were still not skirmishers.
I think this became twofold in how they became more like the Rogue, first with changes to the Ranger, and second, with changes to the Rogue that changed the Rogue from being a Thief type to more a skirmisher themselves.
The idea of them being more of a skirmisher rather than a straight up warrior like the Paladin or Fighter I feel started more with 3.5's version of the Ranger. Here you see the Ranger get less Hitpoints overall then other Warriors (even in 1e, when the Ranger had a d8 HD, they started with 2HD at first level which made them extremely sturdy starting off, and stayed pretty solidly with the other fighters for quite a while in the HP department. 3.5 defanged how tough rangers were in part by reducing the HD to a d8 and ONLY having ONE D8 at first level, thus making them less of a sturdy warrior than others in the same class). Add to that the usage that they mainly used lighter armors and they could not stand up in a direct fight as long as the other Warrior classes.
4e was where we see the Ranger become a solid skirmisher though. This is because the Rogue became a skirmisher and LOST what it was that made them a thief before hand.
The thief has almost always been misunderstood, at least from 2e onwards, with a lot of it starting with AD&D. In OD&D EVERYONE could Move Quietly, Hide behind things, climb cliffs, try to listen for noises, and other things. ONLY a Thief could do these things in almost a mystical manner. They didn't just roll for Moving Quietly, they could actually MOVE completely silently. They could meld into the shadow itself and hide IN A SHADOW of something. They could climb SHEER walls, and other almost magical things. In addition, the original thought is that unless they were challenged or had a challenging situation...THEY SUCCEEDED AUTOMATICALLY!!!
This idea was not effectively portrayed in the AD&D books that came later (and it's possible a lot of people didn't get this idea originally when the classes came out, but that's how it was meant to be played originally). Thus, instead of realizing that these abilities were on TOP of what every other class can do (I mean, come on...do you really think that none of you can try to play hide and seek or move quietly because you are not a thief?) already, they thought only a thief could do certain things. So that Move Silently covered everything on moving quietly. This wasn't helped with the idea that there was an instruction (was it in 2e or one of the BECMI sets?) that anyone could attempt to move silently or hide in shadows at the 1st level Thiefs' abilities.
However, the true dilution started in 3e where most classes, even if it were a cross classe skill, could take classic abilities that were only for a thief. Furthermore, they were not really mystical anymore. It was relegated to the idea of what USED to be considered moving quietly (which would have been a Dex check to see if you succeeded or not, a Thief could, in theory make a Move Silent roll, and if they failed that, then make a Dex check to see if they were moving quietly and if the enemies would be able to hear that). The thief skills were no longer unique and no longer as POWERFUL in any way to what they used to be. They were now...unlike what they were originally intended to be...mundane abilities anyone could really do overall.
Thiefs still kept their trap finding abilities though.
In addition though the Thief lost a lot of their uniqueness, they were buffed up combat wise by changing their backstab abilities into a sneak attack which, in the proper circumstances, allowed them to do more damage.
This was deserted in 4e where certain classes (the Warlock was one at least) that could get ALL the same skills as a Rogue. The Rogue had NO specific roll unique to them in that aspect anymore. Instead they were made more of a combat type character and categorized as a Strikers. They were placed in the same category as the Ranger. Thus, the Ranger and Rogue now shared a similar type of martial role together.
I see that this has continued into 5e, and so, the Ranger I feel is seen more as a skirmisher now rather than an armored warrior in the likes of what you'd see a Fighter, Paladin, or War Cleric. This is due to the role of the Thief itself (with the right background, anyone now can do what used to be relegated to what people saw the thief as doing) not having any really unique roles into itself except being more of a martial character that engaged behind the scenes. They can be also seen as a skill monkey, and though they may be better at skills in general, they don't get those specific skills all to themselves anymore. In addition, they got another combat buff with a higher HD. So now, Rogues are effectively more martial than they were before, and more similar in a role of a skirmisher, like the Ranger has become, than a heavily armored warrior.
The thing is that the Rogue and Ranger both became more of a skirmisher type (and you may be able to toss Monks into that as well, though Monks have done better at keeping their uniqueness than the other two) rather than what they originally were.
Many people today don't see a Ranger as the Aragorn type clad in heavy mail going to battle at the front of the troops, or even a heavily armored King's Woodsman that patrols the Kings forest against illegal activities, that have heavy woodland skills and woodland abilities as well to help them be warriors. They see him more as a bowman or two weapon fighter that has some wilderness abilities and is more of a druidic skirmisher rather than a full fledged woodsman warrior in their own right...at least for some. (Edit: Though you could certainly still try to take that idea of a Ranger in 5e that you did with the old 1e games previously if you want to, there are those that do not see it this way now).
So, if one is seeing a similarity between the Ranger and the Rogue these days, I think this basically summarizes HOW that evolution took place (at least in my current realm of thought, which can be changed by other posts and other ideas).