My biggest issues right now is how do I find good contractors?

One of the biggest reasons these are important is to avoid he said/she said disputes involving the deposits.

And let's suppose that we aren't assuming me to be the second coming of Jesus, a perfectly ethical person who works hard no matter the incentive structure. 

The biggest concern would be how you go from a bridge loan (hard money or otherwise), to a long term fully amortized conventional loan.

Make sure you have a good contractor (my current biggest challenge).

My biggest fear is I will purchase a property and won't be able to rent it at 1k or 900 due to so much lower competition for the same specs in the same neighborhood. 

If you're concerned about late or missed payments in your market consider incentives to make sure payment is received on time, a minor discount, 12 months on time payments = a gift card at Christmas, etc, etc.Also check your local laws when it comes to fines and specific 'grace periods', you may not have much of a choice in the matter.Good luck!

Think of it this way, a lender is the biggest investor in the deal.

The biggest challenge since buying the property has been staying motivated to rent it out.

@Dillon HutsellIt's by far and away the biggest life change you will encounter, but it will teach you a discipline that you take from your military life and incorporate into how you invest.