Go to school? Or keep working?

Question

I have a conundrum here, and I'd love to hear some perspective on the subject.

So my ultimate goal 5-10 years from now is to have $5000/month in cash flow.

I am currently in the military living in Elizabeth City, NC, and I was really set on getting out and going to flight school out in the pacific northwest area, until recently discovering bigger pockets,  real estate investing, and the possibility of taking flight school nearby.

Now I'm having second thoughts on how I should go about the next 2-3 years, so I'm debating 2 options:

Option 1:

-Continue with the original plan, attending flight school in either Hillsboro, Oregon, Troutdale, Oregon, or Tacoma, Washington using the G.i.bill and receiving BAH around $1700-$2100. The entire program varies around 18-24 months, and then add another year or two building flight time at about $30k/yr before getting a job take make anywhere from $50-70k/yr.

-Try to make connections with people in and around real estate investing in those areas to learn from them and eventually build enough knowledge to take action by the time I have a real pilot job.

-On a side note I have thought about house hacking with a VA loan, but unsure of the possibility of that since I'm only living off the BAH and about  20K savings in what looks like higher priced areas.

Option 2:

-Extend for one year (starting from this Sept) and try to knock out as much of flight school as I can.

-I've thought about house hacking in Norfolk, Va area just for the sake of starting somewhere. It is the only area in a one hour radius that has affordable multifamily homes that seem to have good potential of starting  a positive cash flow by the time I move out.

- The Pros of this option are that it seems to be the best option financially speaking- I currently save about $1000 a month. I would probably save a lot more if I wasn't  paying $950/month for my current rent/utilities. Plus the potential of having a cashing flowing rental property by the time a leave.

-The Cons would be having a full time job while attending flight school (along with an associate degree). Most flight schools advise against this to avoid distractions from intensive training. Also the one hour drive with tolls to and from work is doable, but not the most appealing.

What would you do if you were in my shoes?

I would love to hear your thoughts!

Janine Badic · Answer

anything you can do or get while still having the military pay your salary... do that!

As far as investing, remember, when you stop having a W2 job, it gets much harder to get any sort of loan/ mortgage.  Factor that into your investing timeline.

I'm a believer that you should leverage all the opportunities the military gives you until you decide its time for you to go on and do bigger and better things. It's quicker for some than others :) the grass is always greener somewhere but your goal of $5k paadive income is totally doable with some smart investments.

Josh Wilson · Answer

I'm a (very junior) C-17 pilot at McChord AFB in Washington, and while I'm active duty there are three reserve squadrons here that, if you interviewed with them and got accepted, you could live in Tacoma, still do RE investing, and do flight school for free. The flying is incredibly fun (low levels in mountainous terrain, flying down into the Columbia River Valley, etc), and it provides great opportunities to build multi-engine hours and be highly competitive for the airlines down the road. I guess the one caveat to that is you'd have to finish a Bachelor's degree to do it, but it's a well-paying W-2 with a lot of flexibility to allow for investing on the side.

I just got out here, and also just discovered RE investing. I'm working on entering a niche military market, part of which starts at pilot training bases. If you're interested, shoot me a message! It's a long term game, especially with finishing school to go to pilot training, but it's a great place to have opportunities like you're looking for.

Joshua Moore · Answer

@Joshua Hilliard

I am only nearing 4 years, so retirement would be way down the road. I would like to start flying as soon as possible, and if I were to wait for OCS to pick me up, it would probably take 2-3 years minimum before even getting selecting (from what I've seen from other co-workers). Plus the time commitment of 11 years is not appealing to me.  My job in the military is not that bad, I am thankful for the experiences I've had so far, but overall, it is something that is just bearable, nearing total boredom at times,  and I couldn't even imagine staying in for a whole 20 yrs. I would like to have a little bit more control over my life. Money is great, but I value my time a lot more, I don't need much, I'm just looking for ways to end up with a flying job that I enjoy, while pursuing passive income. I do find a situation that is doable as far as finding a house hack to get that started while making decent progress in flight training, then it would be worth staying in for another year or two (I'm still chating with the local flight school at the moment). Otherwise, I would have to hold out for about 2-5 years  before starting a house hack.

Thomas S. · Answer

As long as you can take advantage of tax payers to pay your way keep taking as long as you can. The biggest advantage of being in the military is that tax payers do not object to paying for anything you want. Milk it for as long as you can.

You need a W2 to qualify for financing so make that your priority in prep to leave the military.

Michael Ablan · Answer

Option 1 my dude.  Continue with the plan.  Real estate investing is a life long pursuit that takes a lot of time to do properly.  Get that W2 income and make this your side hustle while you figure out whether you actually like it or not.  You'll have a very difficult time getting started without solid W2 income unless you know someone who will bank roll you, or you have some set of talents that'll make you an attractive partner.

Don't do something you might regret

Melanie McDaniel · Answer

What @Janine Badic said if you enjoy what you are doing  and have life balance and you are moving toward your ultimate goals.

Pull the plug and jump if you are miserable and your soul is slowly dying and you have a plan of action and some support to do the other plan. Ask me how I know.

Joshua Hilliard · Answer

I admire your commitment to your dream. I wish I was so sure of what I wanted at your age. One thing I know though, if you truly want passive income through real estate investing then you are in the right place. The people on this sight are amazing and the values of those running it are beyond reproach. You're in the right spot. Chase your dreams in both your career and investing and don't get discouraged when the hard times come. The rewards on the other side are far beyond anything you could ever imagine. Welcome to BP!

Joshua Moore · Answer

@Ernest Grindle

I have looked into investing in Elizabeth City, and I do think there is some potential right now. I used to live real close to the properties currently listed,  and I would probably not enjoy  moving back into town (I currently live in Camden, way better). Although I'm not 100% sold on the idea, it is definitely worth a look. Honestly, if I had a  choice I would house hack more near currituck or kill devil hills area, but it doesn't look like there would be any places that are available (or profitable if so.

Go to school? Or keep working?

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