How difficult is the city permit? 

The only way to know is to hire a timber cruiser to go out and survey the timber.Value of timber land depends upon how many board feet, what species of trees, the difficulty of getting the logs out, and the demand from the lumber mills.A lot of mills are shut down.

Difficulty in researching prices and especially rents has been something of a barrier to me when it comes to investing out of my area.

If you find the right property where it can be done with out too much difficulty, like in the basement, then you have quickly added value.

Initial Mortgage License requirements were'nt difficult. I

The Carisa and Palma were the first 2 and my building was called Girasol Norte.The only two hurricanes that caused any difficulty in Cancun during my 40 years of ownership were Gilbert in 1988 and Wilma in 2005.

If so how would the difficulty go as far as stretching that money out 

The next time the plan was to pay for e-transfer, but he had some difficulty and thought the previous arrangement would be okay. 

But finding comps is difficult, I will definitely be using near by towns.

Property is rented, credit score 645, having difficulty finding a lender.