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Navigating money issues with lower income roommates

I love my roomies, but while I have a sizable savings account and decent income, they are barely living paycheck to paycheck, even with help from family. Our rent is going up and though they've assured me they can afford it, I'm getting nervous. I don't want to loan them money, but I do want to stay current on our bills.

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Money envelopes have taken over my life in the most overwhelmingly wonderful way

About a year ago, my partner and I — while broke and realizing that our Christmas money budget was about negative fifty dollars — had an idea. We grabbed a few envelopes, and on each one, wrote the name of a bill, the amount it typically cost, and when the bill was due. We put the envelopes in a stack in our room, and with every paycheck, we'd take a bit out to put in the envelopes. But guys, these envelopes, they are taking over my life!

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WTF is renters insurance really, and do I need it?

I live in an apartment, but it doesn't explicitly require renters insurance. I've been renting my own places for four years now, and have gone without it. It seemed like a good thing to have, but not something to prioritize as a working (sometimes struggling) artist. Can y'all help a Homie out and break down what your experiences have been, and any advice you have on renters insurance?