Should I have a Will?

Yes.  You should.  Plain and simple.

Do you want the government to get a big chunk of your assets?  Do you want your relatives fighting over your stuff, your money or your children?  Do you want there to be financial and relational chaos in the wake of your departure of this world on top of the emotional mess that’s inevitable?  If not – bite the bullet, invest a little money, make a few tough, morbid decisions and be done with it.  
While you’re at it, make some end of life health decisions, too.  Do you want to be buried, cremated or have a Viking funeral?  Heh-heh.  I think that’s illegal.  But seriously, do you want your body donated to science?  Do you want to live in a vegetative state for 20 years or have that plug pulled so you can go toward the proverbial light?  
Imagine the shock and grief involved if you’re in the hospital, at the bedside of a loved one who had an unfortunate accident, and you have to decide whether or not to “pull the plug.”  Pretty stressful, right?  Wouldn’t it be easier if you had a handy document that outlined exactly what that person wanted?  Now put yourself in the hospital bed.  Don’t you want to make that horrible situation a little less heart wrenching for your family?
What about your kids?  Who will they go to in the tragic and very unlikely event of your spouse and you dying simultaneously?  
Yes, it is hard to think about these things.  I hated imagining my life without me in such a concrete way.  And if we’re honest, maybe a little part of us feels like if we write a Will, we’ll die the next day.  Let’s deal with that one right there.  There is no cause/effect relationship here, I promise.  It’s understandable, kind of, but totally irrational.  
Another reason people avoid doing this is they say “I don’t have anything – I’m not rich.”  While that’s the case for most of us, you probably do have some things – antique hand me downs, a car, a life insurance policy, a 401k.  Plus you should certainly clarify your wishes about what is to be done with your body, your pets and your children.  
I have cancer.  So that lit a fire under our arses.  But really, we should have done this years ago. And so should you.  After having gone through the process with a kind, skilled attorney, I feel relieved.  If I’m driving down the highway and a semi veers into my lane, my last thought can be something more poetic than “Oh, $hit, I should have gotten that Will done.”