Newbie string questions

[KUNGfuSHERIFF]

Greetings, all.
Earlier today I restrung my bass for the first time, using Helicores. I remember reading that, when winding gut or synthetic strings, the string should not come into contact with the sides of the pegbox. Are there any such restrictions with steel strings? Is it OK for string that is wound onto the machine to cross over itself, or is it best to wind the string neatly?
Many thanks in advance.

[Jake deVilliers]

Steel strings also need to be kept from wedging against the cheeks and cracking them.

There's no need to put all of the string on the string post - pull the extra through the hole and either tuck it in or cut it off. You only need about four wraps on the post. If you overlap, you'll change the tuning ratio where it goes over the lump and that's annoying!

[KUNGfuSHERIFF]

There are definitely more than four wraps. I'll trim and re-wind. Thanks for the guidance.