I'm personally of the opinion that it's generally best, at least for buy and hold properties, to have more equity in the deal, but as someone who lives in California, buying local properties with 30-100% down is fairly difficult for the investor just starting out.  

Many banks require a year or two tax returns showing that you have experience managing the properties which may be the most difficult thing depending on how long you've had them (your income itself really shouldn't be a huge factor based on those numbers)Your existing properties could be offered as collateral as well, but that's a bit higher risk and I wouldn't suggest it.Another option would be to "house hack".

Meaning, what happened that you totally didn't expect to be so difficult?

I would like to get started with wholesaling, which I know is currently very difficult in the Colorado market.

They're about 80 pages long and difficult to interpret.

If you are going to inhabit the property, a 203k loan will provide financing for the purchase and renovation, but I hear that those are sometime difficult to work with. 

If i'm hearing you correctly you are saying it is more difficult to get financing if your 1099 than W2 if its a brand new job?

And yes, that is the most difficult - guessing where it would go between now and the time we buy - up / down / nowhere and by how much.

If you can find a deal of a house it probably would cashflow well but I feel like the markets a little overly inflated which pushes prices up and returns down making a deal more difficult to do(prices around 140+).

There is so much information that it's difficult to determine what is important to remember and what is not.