I could be off base but that's my take on it.1,500 is not a lot for someone who could actually teach you the business.. but you may want to talk with some local folks and offer to work for free in exhage for some education you may have some takers on that.But at your age I personally would spend the money getting a RE license and go to work for a top producing broker on a team and REALLY learn the industy.. wholesaling is not a life long pursuit with most folks...

I was pretty stringent about following rules.

That is very good.Repairs will depend on the tenants and on the effective age of the building.

I am 34 years of age with a high desire to break into Real Estate as an investor.

It's amazing how many tenants go the rent-to-own route & the RTO companies call me for a reference.Often if we do a flip or sell we will move our own aging appliances to the flip & the wife gets to pick new ones. 

It will help you actually take action and buy something otherwise you will spend ages trying to understand everything which is impossible. 

I would love to hear any advice you guys have for someone my age getting into this.

The average culprit is not an evil corporation or foreign investor - The typical tax evader in the United States is a male under the age of 50 in the highest tax bracket and with a complicated return, and the most common means of tax evasion is overstatement of charitable contributions, particularly church donations.  

Congrats on looking into REI at such a young age.

I need to be certain that at the legal age of retirement my wife and I will be able to TRULY  retire...if we choose to do so.If we was to sell our primary now, we will be able to pay off all of our consumer debt, student loans, with money left to invest.