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!

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.

Lenders won’t accept income from the GI Bill as income for the purposes of VA loan qualification. This is because the VA loan lending guidelines doesn’t count this type of income. If you want to get started investing now stay in. If you want to build relationships and go full time with school get out.

Also, make sure you claim everything that has broken on you since joining the military. I have back problems and pretty bad tinnitus that got me VA disability. If you have even 10% in disability you get the required funding fee waived.

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. 

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

I think I'll take the next week or two to try to get a feel of what option 2 would be like. I'll try to meet up with some of the flight instructors in this area and I'll drive through the neighborhoods of potential places I wold like to house hack in. If don't like the idea of option 2 by then, I will stick to the original plan. 

Thank you all for all of your responses!

@Joshua Moore, going with option 2, have you looked into investing in Elizabeth City? You could house hack for your final year.

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.

I have a question. How much time in do you have? If you are over the hump for your retirement I'd advise staying in then pursue your flight school and real estate investing after. Those retirement benefits are worth their weight in gold. I know this because I'm there brother. If you have only been in a few years then why not go to flight school in the military? Get paid to go to school, make way more than your income cap of $70k, and retire with experience and a pension (passive cash flow). You can invest the whole time with your W-2 income and your VA loan intact. Don't throw away that military time. As someone who knows from personal experience, maybe consider some other options. I think you have cards to play that you didn't even know of.

Typically going to school is your best option

@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.

@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. 

Originally posted by @Joshua Moore :

@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. 

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!

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, I’ll PM you today. I was considering a very similar path. I’ll give you some considerations as a long time soldier and WA state resident. NOT YET an investor though, in the spirit of full disclosure.

Josh Wilson I’m a soon-to-be retiring 1st Group guy also just getting into it. If you’re up for a coffee one day, message me! Would love to chat.