1. Shards like Atlantic still have high population, but some are really low, like several of the west coast ones.
2. It really depends on the character type. Some skills are easy to train (combat skills), some still take ages (taming & bard skills), with a few just being tedious (crafting), but the real limiter is if you taking skills from 100 to 120, and have to get the money to buy the powerscrolls to increase those skills' caps.
There are also Alacrity scrolls the give you 15-minute bursts where you gain 0.1 to 0.5 per gain earned, and Scrolls of Transcendence that give 0.1 to 1.0 (and means to combine them to where you'll see 2.0, 3.0 and even 5.0 SOTs for sale, though the 5.0s are usually drops from a high-end mob).
With changes to the monsters, and to Shame dungeon (part of a long-overdue dungeon revamp), you should be able to find yourself in a position to where a fresh weapon-using character is challenged, but still gaining skill, and work your way up to tougher monsters as you go, as a form of "in the field" training. Ask around on the shard you choose to play on, and you will probably find someone willing to act as a guide.
3. Out of my area of expertise - but, from listening to the trash talk, getting the skills will take you a few weeks, but to be able to win, you'll probably have to get the right equipment made for you or looted, and depending on how many tens of millions of gold you might have squirreled away (it's possible in high-end PvE to make a few hundred thousand an hour, these days), it might take you a couple weeks to a year or more to get the perfect suit for you. Some outrageous stuff is coming out of Shame right now, if you don't mind it being low durability and cursed, and next publish brings a new form of crafting enhancement with the potential to make suit quality start shifting again.
4. There's been a lot of content added in the last 2 years, and older stuff made a lot tougher. What the complainers tend to be complaining about is "their" stuff not being changed, and acting like the game styles and content changes/additions aimed at other players don't exist, because the changes weren't for them personally.
One thing I found hilarious were the supposed "old-timers" who whine for the "good old days" before Trammel, yet apparently couldn't remember that the Golems, controllers, Juka and Exodus stuff were NOT the original spawn of Wrong dungeon (they displaced the original spawn between the release of 3D/LBR & Age of Shadows, several years after Trammel), and screamed about the "real" Wrong spawn being removed a few years ago (when in fact, it was just returning the original spawn to the dungeon - though next publish will be replacing that spawn again with nasty tough spawn like with the Shame revision).
I swear - some people will complain on Stratics and UOForums just to hear themselves complain - like some of the really prolific Posters, and the Other Prolific Posters that Seem to primarily post in replies to call the first posters idiots, without actually looking to see if the first poster's idea has merit (which, often, they do have some merit, but are phrased usually in manners to deliberately incite stupid responses from the attackers).