@notsonic: You sort of jumped between a lot different questions here, so I'll try to tackle them all as best I can.
You are correct, gear with light on it will increase your level. The expected path in the vanilla game was, upon hitting level 20, for you to run daily bounties, run strike playlists, and play crucible. Doing all of those will gain you reputation, which will put you on the path towards reaching rank 2 in both crucible and vanguard , which is the rank required to purchase legendary armor. All non raid legendary armor has the same amount of light on it, which in the vanilla game would get you to level 28 with a full set (29 if you had one exotic piece and three legendaries). Full raid gear (or three pieces of raid gear and one exotic) was the only way to reach the level cap of 30.
Also, both crucible and strike playlists drop rare armor, which can vary in light level, but the maximum level attainable from rare armor in the vanilla game was 26 (which is also the level of normal mode for Vault of Glass). The idea was that, as you were working on gaining rep to buy legendary armor, you were also slowly picking up armor that would take you through the low to mid 20s, opening up higher level strike playlists and allowing you to tackle the weekly heroic strike on the lower and middle difficulties to earn strange coins to buy exotics from Xur. It may take weeks to get full legendary gear to reach level 28, but not to go from 21 to 22 as you say, you'd reach that after your first handful of strikes or crucible matches, give or take based on RNG. If you were super lucky you could even jump to 25 or 26 shortly after hitting level 20.
With that said, if someone wasn't aware that focusing on gaining the rep to buy gear was the most efficient way to level up (which is really is, rank 2 is pretty quick to get, and after 2 weeks of capping your crucible and vanguard marks for the week you'd have enough to buy full legendary gear), it would be very frustrating. That's why things like the loot cave were such a big thing back in the early days, since legendaries didn't drop randomly that often, people did whatever they could to attain them. The smart players back then knew that earning marks and rep was much more efficient than shooting into a cave for hours on end, but most players didn't realize that.
As for how new players attack the DLC, neither expansion opens up until the mid 20s, but the ramp up has been significantly quickened since the early days. With the dark below, the new raid gear took you to 32 (level cap), the vendor legendary gear took you to 31, and rare armor drops could get you as high as 28 (the original non-raid legendary level). There are also legendary gauntlets that drop as a guaranteed quest reward for one of the optional DLC quests. With the House of Wolves, things are even easier. Vendor legendaries take you to level 32 and rare armor can get you as high as 30 (which means you can conceivably do hard mode Vault of Glass at level in all rare quality armor).
House of Wolves doesn't have a raid, but "end game" gear (from Prison of Elders and Trials of Osiris) will get you to level 34. You are correct that you can upgrade your current stuff to level 34, but only legendary armor. Rare or lower quality armor can't be ascended. Additionally, the material required to ascend your stuff only comes from current end game content. As to the point of getting new gear, it's about the bonuses. The new gear system allows to prioritize min/maxing your gear and shooting for the perfect stats and bonuses for your playstyle or for specific types of content. Rather than just relying on whatever raid armor you happen to get and rolling with that because it gets you to the cap, you can choose your armor based on the perks and just ascend it. The end game gear also starts at level 34 and comes with an extra bonus (in the case of Prison of Elders, ones that specifically affect that content) to set it apart from vendor quality gear.
To your question about random drops in raids, it was really bad in the beginning. The drop rates for Vault of Glass, specifically armor, are very low. The drop rates were so low that people were creating multiple characters of the same class so they would have multiple chances of getting loot for that class per week rather than run three different classes and spread the loot around. I know I personally ran Vault of Glass about a dozen times across my two warlocks before I finally had the gear to reach level 30. To put it in perspective, there are 4 encounters in VoG that can drop raid armor and you need three pieces of raid armor (if you have an exotic as well) to reach level 30. That's 48 potential drops to get 3 pieces of armor. I definitely got duplicates, but I didn't have a full set for quite a while (If I recall it was the gloves that eluded me the longest). It also didn't help that the helmet only drops on hard mode, which was incredibly difficult as a full team of level 29s.
With Crota's End, the second raid, they significantly increased the drop rates for armor. I had all three of my characters fully outfitted in Crota's End gear within the first few weeks after The Dark Below released. With HoW, the reliance on RNG is lessened even more. You are guaranteed one piece of end game gear and one end game weapon from Prison of Elders each week, with a chance for more, as long as you run each of the three challenges. You'll also get two of the material used for upgrading old gear. Trials of Osiris is less of a guarantee, since it requires being good at PVP, but one piece of gear and one weapon would be a guarantee upon reaching certain win milestones, with even more possible for 8 wins, and a windfall of loot being offered for 9-0 runs.
I'm not familiar with raiding in WoW (never made it to that point), but I do remember hearing long time WoW raiders trying to tell everyone during Vault of Glass that this was what raiding was supposed to be like, and running it over and over for the chance of getting gear was part of raiding. Whether or not the drop rates were in-line with raids in other games, Bungie certainly realized it was too punishing for the more casual game (compared to MMOs) Destiny was meant to be.
As for what's next, some of the leaked data for the fall expansion, which is supposed to be much larger than the previous 2, suggested that the XP level cap will be raised 30. As I explained above, the past two expansions have increased the easily attainable level cap (vendor gear) to match or even exceed the previous raid level cap, along with introducing a new end game light cap. If the leak is true and the XP level cap will be raised to 30 in the next expansion, it will be easier than ever to be capable of seeing things like Vault of Glass and Crota's End. Of course, the new raid will probably be somewhere in the 40s, and the new light cap may be as high as 50.
However, none of that is confirmed (we'll probably know a lot more at E3), but with each new expansion Bungie has made it easier than ever to level up (legendaries drop like candy now), so they have certainly made it easier for new players to get into the good parts of the game quicker.
Hope that helped.
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