What would you do if you were in my scenario?

[Drake Johnson]

The questions you’ve all heard a million times... What should I do? Or, what would you do?

I’ve been in the military for almost 5 years now, and will be getting out soon. Prior to the military, I did concrete work, drove a truck (I got my CDL when I was 16), and operated heavy equipment. I know that I want a career in real estate, and am willing to work hard for the next few years to become financially independent.

Here is my plan:

Jan 2020 - March 2020

Buy my first property, located in NC, while I’m stationed in Okinawa, Japan… Read the rest, and please tell me why I should, or should not wait on buying the first property

This is what I will be leaving the military with (May 2020):

If I don't buy a property, around $100k ($25k of which is in a Roth IRA)

The GI Bill - allows me to go to most public universities for free for 36 months, and provides a monthly housing allowance.

July 2020-May 2021

I plan on attending trade school for carpentry in the fall/spring semesters. Also attending an electrical course in the first semester, and a plumbing course in the second semester. This way I can be the ultimate DIYer and have the ability to evaluate whether contractors are doing things correctly once I’m ready to start using contractors. During those two semesters, I will also get my associates degree in real estate online.

This will cost me around $12k since I will more than likely not have time for a job, and won’t receive enough housing allowance from the GI Bill.

That leaves me with about $88k to start REI, or less if I buy a property now.

May 2021

Move somewhere the market makes sense for BRRRRs, (Jacksonville FL, Columbus OH, ect.) and start BRRRRing properties

-I'll need supplemental income, so I'm looking for that "rare and valued skill" to pay the bills until I get $3000/mo in cashflow to be financially free. I know real estate agents and contractors are not rare, but the rockstars are rare AND valued. I'm thinking about contracting specifically for investors for my supplemental income, or getting my realtor license since I will have the education requirements done. Does anyone have other suggestions for those valuable skills that I could do part-time while building my portfolio and enhancing my REI skills in general?

Thoughts on buying my first property now, and other considerations for supplemental income in the future?

Any input would me greatly appreciated