I always think earning the passive income from rental property is a very good retirement strategy.

If you desire to be handheld, then it really is beneficial to join a real estate association and pay to join their mentoring program OR even better, find an Investing Agent that does Wholesaling and ask them to guide you through Wholesaling in return you'll use them in representing you so they get paid. 

Second, I'm not sure about the ARV as I am currently a buy and hold investor, therefore, I'm not looking to improve the property to sell, but to make it a desirable living place...which I learned quickly are two totally different animals.  

If I had to buy in a higher priced area I would do the same thing except use my "earned" funds for a down payment so I could acquire more and set them up to be paid off within 10 years with my cash flow.

If you're self employed, you're undoubtedly deferring taxes on some of your earnings.

Yup, but it helps.It is a simple decision, but has to be based on your own internal needs and desires.

My desire is to obtain multiple SFR to rent and possibly flip.

You don't want to push the wholesaler away, because the deal is still feasible, but spending less is just as important as earning more in this game.  

And if you drop him, you would be depriving him of the chance to earn the commission he has been working toward.

I think for me at this point, is more for feeling secured that we live in an decent area with a kid, not the most desirable area, but decent enough and also close to work.