Since you're in Texas, I'll use a town like:  Each town will be different based on the population living outside of town. 

The 10k is the difference in the points.With lender 1 will cost 10k more in points.Lender #2 is kind of unknown.

There's many different avenues you could take.

The only difference on paper is that the deductible for hail and winter storms is 5k instead of the 2,5k that I have with Farmers. 

How long it takes to be financially ready is different for everyone.

Chicagoland as a market may appreciate at different rates, and property taxes certainly do not help the cause.

If I had stayed at UNT I would likely have majored in real estate and gone down a different path.

The times were different then: rates were incredibly low and property values were steadily rising so even if I overpaid for a property (which happened a few times) the market usually bailed me out.It's a very aggressive strategy and as others have said, if it doesn't go right then there is a lot of risk.

Like I've said in my original post I understand all the different methods and reasons for each.

A good lender who understands out-of-state investing can also make a big difference.