When I met him in 2010, he told me how he just finished a book (Rich Dad, Poor Dad) that spoke about reaching and attaining financial independence.

My goal is to make around $25k-$30k in commissions , per year.Is my goal attainable?

This is still on the radar for experience purposes, but I have started reading highly rated books, attending PIN/REIA meetups, making solid headway to attaining my realtor's license and looking at the markets more and am eager to be successful using BRRRR. 

Are we looking at testing max home prices that can be attained and then staying at that level till inventory catches up ?

"This, however, was afterwards of use to me, the impression continuing on my mind; so that often, when I was tempted to buy some unnecessary thing, I said to myself, Don’t give too much for the whistle; and I saved my money.As I grew up, came into the world, and observed the actions of men, I thought I met with many, very many, who gave too much for the whistle.When I saw one too ambitious of court favor, sacrificing his time in attendance on levees, his repose, his liberty, his virtue, and perhaps his friends, to attain it, I have said to myself, This man gives too much for his whistle."

What I am hearing is you hired an architect "just to submit a few plans to attain permits," correct?

It entirely depends on being able to actually attain a great ARV (supported with an appraisal) for resale or to cash out refinance.

Try your luck right outside the city for more easily attainable gains.

They do have a minimum number of listings if you want to attain Premier Host or SuperHost status....

@Dale Graham The advice given to Read David Greene's book, "Long Distance - Real Estate Investing" is great.My Personal strategy and what I find to be the most popular (and attainable) will be compromised of Metro Detroit suburbs.