Keep Tooling Leather Malleable?

[jk215]

I finished my first project last night and came across a few problems. The biggest was my leather drying out and cracking as I made holes with my awl. After some research it seems I need to keep the leather well oiled and have some neatsfoot oil on the way. My question is what exactly is the process for applying oil? Im assuming it needs to be applied after dyeing but when else? Do I apply it before I even start doing anything? After finishing? How long should I let it set in before buffing? Any help is appreciated!