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You get bonfire warping roughly halfway through the game. Based on just about any route, meeting Andre the Blacksmith happens fairly early. I'd wager it to be less than 1/5 the way through. You have a handful of areas + bosses to go, but keep on! Exploring the world without teleportation can be quite fun; especially on your first or even second run. The later games really pamper the player with that kind of thing, which can make sense because of their expansive worlds. But, I quite like the fact that it isn't immediately available at the start of the game for Dark Souls 1.
TL;DR: You're a long way from teleporting, but in the meantime keep leveling and upgrading your gear. You'll get there!
Question 2:
From my experience, Wulf's DSCM (one of the originals matchmaking mods) had around 1100 - 1400 people using it most of the time before the release of DSR. These days, the remaster is still pulling at least 1100 (dropping to around 7-800 at night). The remaster does just as well a job as the mods did, and it works right out the box. Very user friendly in that respect, which lends itself to larger usage imo. The release of the remaster split the DS1 playerbase mostly in half; and I, myself, tend to gravitate towards the remaster. In the time since its release, it's still pulling great numbers. Also, setting region to global (in network settings) may help you find partners if you're still struggling.
TL;DR2: I won't speak for everyone, but I play the Remaster more frequently and I'm sure there are many people who feel the same way.