[Seahawk]

Is this a 1099 position Matt?

I am not sure exactly what you are referring to when you use the term "contractor".

If it is a 1099 (no benefits, withholding, etc.) I can give you some pointers, things to avoid, etc.

If you trust your former Boss and you like the work, it can be worth it if you are careful and know the pitfalls going in.

I hire 1099's all the time for short fuse, high burn jobs. but most of those guys have specific skill sets and are retired from another career.

Make sure the level of effort is there, the time of the work is specified and that there is customer money attached.