I'll write a quick description of each system I considered and why I used or discarded it.The winner:- Xero is what I am plugging forward with (thanks for the recommendation @Gita Faust .) 

Might be interesting for software that would take a typical REI model and plug in the variables and spit out the output numbers....speeding up the analysis.

If your assumptions are correct and you can increase rent by that much and actually book the place, pull the plug immediately.  

It’s not perfect, but I’m fairly certain I can get my living expenses around $1k living with a roommate and I can bust butt to regain savings to buy a pure rental property.In addition, we are seeing a huge influx of people from DC, NYC, LA, and Austin.

Waiting too long could bite you in the butt.

Just plug your estimated repair costs, however small, into the above example and you'll get an idea of what the cash requirements would be.

Most have boutique underwriters in their portfolio that can usually kick the big guys butts in price/performance. 

Does anyone have a recommendation for a contractor in Crested Butte/Gunnison Colorado?

I'm in Crested Butte, CO, and as much as I'd love to find an investment property here, I would be starting with negative cash flow, most likely 30 miles away in Gunnison, CO.

worked my butt off.