Goal is to one day retire from the service and have a few properties already under my belt (fingers crossed by the end of 2020) to jumpstart a second career.

My sister has great credit and has had a stable job for a long time, so I'm assuming she could co-sign the loan for me either way (FHA or traditional).

IRA is an Individual retirement account, it is set up for individuals, not attached to any company or employer.

There are many folks nearing retirement now who are leery of the stock market turning down when they are close to quitting their day job and needing that money. 

I also benefited from Gary Eldred's "Investing in Real Estate" and Chad Carson's "Retire Early with Real Estate."

What are everybody's thoughts related to the Baby Boomer retirement period we are currently in, and its affect on the real estate market?

I have a pretty high earning capacity currently but would like to retire in 5 years.

It sounds like you don’t need the cash flow currently and are more concerned with retirement in 7 years.

He realized that he didn't have enough to retire on & as an aging contractor his company was starting to lay him off over the winters.

You are twenty, if you are working while in school and have potentially low costs of living put as much as you can into investment accounts that will grow exponentially, look up Financial freedom retire early as concepts you can adopt and start early, look for house hacking opportunities (aka find a home you can potentially partner with someone to buy or rent in your area with a decent amount of bedrooms, and then rent bedrooms out to friends) Anyways, learning how to put away a majority of your earning into things like Roths, Self directed IRA's or any other potential growing tool while you get your degree in your respective field/ go into working in that field will open up so many doors for investing in 5 to 10 years.