One problem you are going to run into now is if you had your cousin go see the property and he or she saw it with the listing agent, the listing agent now has procuring cause, with you as their client, to the commission on the buyer's side whether you choose to use another agent or not.

I’m a veteran, so I used a VA loan to procure my mortgage.

A thread like this will invite some person to give a boiler plate response like "Your property management should make you more money" (which they're probably parroting from some podcast they just listened to).There are a minority of stellar property managers, but the vast majority are either 'meh' or major sources of incompetence and liability. 

I can afford to put 20% down and get a conventional loan, but should I really be considering an FHA Loan and putting something like 5% down and using the other 15% towards procuring another investment property?  

He also took it upon himself to repair some old equipment for us (parts procured on Amazon) that we were ready to dump as useless & worn out.

How do you differentiate between an owner occupy and an investor during the procuring process??

Are there any resources or best practices when looking to procure such services?

I've been asked by a family friend to invest in a commercial deal in Bensonhurst Brooklyn, NY that they've already procured.

It is my goal to procure another property by the end of this year.

Looks like not only a good business model by itself, but a great way to procure buyers.