Now if your thinking location jumps out as a big factor to all this, you hit the nail on the head, location location LOCATION. 

So I just joined Buildium, spent hours setting everything up, it seems mostly pretty great, except one HUUUUGE issue that is making my head explode...they don't support credit card tracking?!?!?  

Even thought we headed out at 11:15.

People just make sure they have all that they need when they head out.

Then reality hits and you find yourself in over your head.

Heads in beds means more revenue.

Obviously would be a slower process, but would create very little debt hanging over your head.

Thanks for giving me a platform to word vomit as I rattle around these under-formed thoughts in my head! 

Anyways, I think @Caleb Brown hit the nail on the head.

I always recommend starting with a prequalification letter to get a solid view of your purchasing power before heading out into the real estate market.