Case in point, every time I had to send money into school with my sons it was always a major production because none of the things I needed (envelopes, pen, paper clips, etc) were ever right where they should be. Here's one example of a super simple system I now use when sending notes/money to school with my guys.
I'm sure you are all well aware of my hoarding issue by now. However, unlike the hoarders on TV, I actually use my hoarded items. I have an old calendar holder that I kept long after the calendar had expired. Here's how I converted the leftover board into a school envelope system.

In addition to the calendar holder, I also reused an old folder to hold the envelopes.

I simply cut out the shape of the flaps...

And then hot glued them onto the board.

I also cut an additional piece of the folder and attached it to the board to hold paper clips and binder clips.

Here's the finished product...

And here's the envelope that I made for school...

My guys have been in school for three weeks now and the envelope system is working like a charm...no stress!
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