Go to school? Or keep working?

[Joshua Moore]

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!