Monthly rentals in cities:
 

If you're away for 1-2 months at a time where do you normally shack up? Internet connection is a must also.

Monthly hotel rentals? Short term condos? Any suggestions?

I always look for vacation home rentals. Not only does my elderly dog like having a yard but having a kitchen means I don't have to eat restaurant food for a month at a time.

vacation rentals over hotels. I look into this anytime I'm going somewhere for more than 2 weeks. yes its usually cheaper, but you also get more of a "home" feeling than living in a hotel room with a 32" TV

I'm good at this one, assuming you're traveling to foreign countries and not staying in the West. If that's the case, all you do is rent a moderate hotel for a week over the internet. From there, you can make your contacts with locals, look through newspapers, look at notice boards in town, look for "for rent" signs, visit local rental agencies, etc.

From there, it's almost always easy to get a good place for a good price. For example, go over the internet, you'll get some 300sqft studio hotel room for $3000/month. Spend a week looking around, and you get a 2bdrm apartment, fully furnished with full kitchen, in a nice area for $800/month.

I think that would be totally up to the location you are looking at ?

This is more for big city living. 2 months at a time around. Im not to sure if they have standard vacation homes in bigger cities but i could be wrong.

This one would be for Montreal per say and more western cities. I found some quality prices using craiglist for short term rentals. Im just wondering if there is a better way to go. I could for sure look around once i am there. id just rather be set up shop before hand. but i can swing it in a hotel for a bit.

You can get a local Renters Magazine. The magazine has a list of prices of rent.