Welcome back!

1- I don't know much about which server is best so i can't really help you with this.

2- You play the race/gender that you want. I think the majority of players do not care, it's your character and you can play whatever race/gender you enjoy looking at for endless hours. Plus, I am pretty sure that more than half the miqotes are guys in RL.

3- I like Gridania, it's where i am most of the time but Ul'Dah is still the place where everyone is the majority of time and where the trade happens. Altho it doesn't matter much where you start, once you start doing rank 20+ leves for marks, you will have to go to the city where that specific guild is.

Also I started over with patch 1.18 and started in Gridania again, I enjoy that place

4- You get some gears from leves and low level items are not really expensive (on rabanestre anyways) and gils come more easily the higher you get. It's always good to level a DoH or 2 if you don't mind it and enjoy it to an extent since it helps with repairing gears as well.

5- I leveled DoM exclusively and don't have a problem with it.

With all that, welcome back again and I am sure you will find the game changed a lot a lot more fun to play.

~Cheers