I am not a tech person. In fact, I am still pretty new with gears myself.
But I think some of the very important questions have to do with yourself rather than the mic. Namely:
- Budget
The most basic question, of course. How much are you willing to spend will help you determine what NOT to look at.
- Frequency of use
Second most important question. You can get a mic for 300 bucks and have it busted the very next day if you're the kind of guy who goes all over the isle on a skateboard.
Also, consider the kind of crowd you are up against eg sweatier crowd=more humid place=more prone for your mic to show signs of succumbing to scrap heaven.
- Style of singing
Are you an RnB/Jazz singer? Rock/metal? Screams even? Does your voice lean towards the lows or the highs? Answers to these will help you decide on the type of sound you want captured by the mic ie bassy-er or trebly-er. Frequency range plays a certain role here, although considerably lesser than in studio environment.
Again, the style of singing can be detrimental to your mics usability. You already are thinking of lugging your mic around, so durability is key here. If you are a screamer type, you want durability x 2. High SPLs can damage a lot of lower quality mics. Even high quality condensors will be shot if you scream into it.
- Other misc consideration
Something as simple as colour and the availability of an on and off switch can be a source of discontent to some folks.
That being said, I would personally recommend the SM58 because of reputation, build and sound quality at a reasonable price. It's my first real mic; a tremendous improvement from the 2 cheap karaoke mics that I had been using prior to it. I like the fact that it feels rather 'heavy' (read=solid) in my hand. Good for recording and performance.
Alternatively you can check out Sennheiser Evolution 800 series mics.
There're also 3-pack mics ie 3 mics in a package deals: Samsons Q6 and Whaferdale's DM series are pretty good value.