It sounds like you navigated the challenges well and gained valuable lessons for your next venture.

As I continue to gain more knowledge, I am intrigued by the opportunities that real estate investing can afford while on active duty. 

- If so, 1031 into something bigger and easier to manage and then when you pass, the inheritor receives your property(s) at a stepped up basis - subject to Inheritance Tax limits.Otherwise, sell one every 1-5 years when you need the cash, so you can plan expenses to offset capital gains.

As you gain experience and tackle even bigger projects, you'll realize that what once seemed like a mammoth deal becomes totally doable.When it's crunch time, there is no room for improvisation.

I am excited about gaining more knowledge and deals! 

Are you trying to hand your “friend” a 50% taxable gain that you’re going to keep?

Quote from @Melanie Baldridge: Why I like investing in real estate more than 401(k)s.Both offer tax deferrals, but here's the difference:If you're making pre-tax contributions to your 401(k), then withdrawals = ordinary income tax.With real estate gains, you're paying capital gains tax (which is typically lower).Plus, RE investors get:1.

Just a few tips to look into but it usually takes some time to gain steam on your first listing so be patient and keep analyzing the local compeition /your own listing. 

My advice would be to start small with your first deals to gain experience before scaling up.

Depending on comfort and cash, it might be a viable option as you can build equity and then sell without having capital gains, assuming it's your primary residence and you've lived there for 2 years.