However, we were basically gambling on every transaction at this point in our career.

IMHO,  whats important is to walk the property, otherwise, you are taking a vegas gamble with not being able to see the inside. 

Colorado and numerous counties have been imposing restrictions on nightly rentals and continue to get more restrictive.

If you're really just getting started and you are trying to narrow down a list of potential markets, there are numerous publications that provide reports on everything from employment to housing to trends to major changes within cities, etc.

@Dylan Cook There are numerous lending products available to investors.

I have owned numerous businesses spanning 37 years, including marketing and management consulting, lawn care, landscaping nursery, horizontal directional drilling, heavy construction, and reclaimed wood.

Every time a tenant moved out 3 out of 8 evictions or so, it felt like a gamble, with someone leaving the place in ruins. 

There are numerous variables to take into account in this scenario.

my problem is I have not found anyone who will look at the deal until i have it under contract so I dont know how it will go and I am speculating as to what I think it will go for.I don't have 500 or a 1000 to lose on a gamble.

Furthermore, when putting in offers on houses, having numerous prequalification letters might give you more negotiation leverage.