Hey Cabron!
Picking a coin can be tricky. You can go high risk and shoot for the projects that sound like they're offering a great product, but you'd be accepting the fact that what you earn could go up in smoke if you plan to hold. Or you can go with a higher market cap coin. What's your objective - to hold some bags of coins and pray for riches, or to play it safe and continuously earn over time?
Once you can answer that, you should be able to narrow down your searches. And then you can narrow down the miner to use.
Operating system choice comes down to where you feel comfortable. Regardless of the operating system you choose, keeping your rig online 24/7 is important. Downtime == no profit == long time till you recover your investment.
I'm a developer on the project, so naturally, I recommend
Foreman for monitoring. It works on both Windows and Linux, it's open-source, and you don't have to worry about giving us control of your rigs - we are minimally invasive while other products want free reign.
Best of luck in your hunt!