Beginner guide - How to start digging?

First, you have to know that since the update against RMT, you cant dig more than 100 items, that takes around 20 stacks, depending on your luck.

I recommand to be at least whm 38 to be able to teleport yourself to any zone.

Start by buying Gysahl Greens in a nation town, or in Rabao. Because if you have highest fame, it will cost you 62 gil instead of 68 in Jeuno, and when you buy 20 stacks, it makes a little difference (14880gil instead of 16320gil, at the beginning, it's important to try to not lose too much money).

Dont try to dig directly in zone with high profit, you will lose your Greens for nothing because higher rank than you will certainly be in those zones. Try the zones for Skill ups, listed here.
And check the current time before going to dig, if it's "Waxing Crescent", dont go, high level diggers are digging mostly at that moon phase to dig Elemental Ores and you will have hard to dig someting.

I dont think that you need to invest in chocobo riding time gears, you will need to change zone and then change of Chocobo.

At the beginning, you will mostly dig Bone chips, keep them for money at AH (try to sell them in Windurst where the Bonecraft guild is and less fees than Jeuno).

Keep in mind that you will certainly lose money at the beginning, but after two years (if you dig until fatigue every day), you will be capped! (it's not easy, with other diggers, the other things to do ingame, your own life etc, you will certainly not be able to dig every day).

If you dont like to dig, just dont do it, sometimes it's annoying to get nothing and if you cant handle that, just find another hobby :)

Good luck.