Gear and level are similar to how 11 was when it started, just the scale is different. From 1-20, you can go with a basic set (such as the Onion gear). Otherwise, leve drops are decent, but rare, it will take you longer to get to level 20 than to get gear from leves.
At level ~20, you can get gear from the low level dungeon. It takes time, however, with some help it can be easier to get, and you get exp while you are farming your armor.
After 30, you get the totorak and NM gear you can use until 40. At 40, you will most likely end up at the wards fishing for gear, and wishing you had the millions of gil that people think you should have.
Dated gear has better stats since it is INCREDIBLY hard to make, and that is what you get for the effort. However, attaching 1-2 materia will make the non-dated gear better than the dated gear very easily, however, if you are just starting out, attaching materia on your own requires you level a craft you probably don't want to deal with.
But, as LillithaFenimore pointed out, a good LinkShell can help you with most of this stuff. Though, getting a linkshell that isn't solely focused on Ifrit and Moogles can be difficult. Though there are more people popping up all the time now (at a trickle mind you), so finding people your level should be possible.