Sell it off for a onetime payday at a high tax rate  only to have to do it again to eat again. 

I recently quit my W-2 Job an am now having difficulty being approved for even a small conventional loan and looking for advice or tips. 

The low interest rate I cannot give up especially since rates have risen quite a bit since then.The place will be my second short term rental property. 

The winters can be quite slow (and we have a long winter) even for the hotels. 

I am definitely looking to network and learn with individuals that have been in REI for quite some time.

There is quite a difference between the two.

Renting out a $1M property once you leave it is not going to generate any cash flow for you.Take your $300k and invest it in rental properties out of state and use that cash flow to pay for your rent or to quit working your day job and move someone cheap!

I just got a listing agreement for a duplex in the Gladeview area today for $215,000 and it is the cheapest duplex I've seen on the market for quite some time.

OC is really expensive and I am afraid that your saving and income will be quite challenging for you to qualify for buy and hold.

I agree with the above poster- don't quit that job yet, it will provide you capital to get started.