@Jake ArnoldYou've really got a TON going for you and sounds like you can stack together multiple strategies which will ultimately really accelerate your growth.1) You are willing to move2) You are willing to rehab yourself3) You are willing to house hack with roommates4) You live in/near markets that cash flowYou are perfectly setup for owner occupied house hacks of multifamily properties with a possibility to transition to BRRRR or live in flips once you have enough capital.I firmly believe it's important to play to your strengths and what your market(s) allow.

Is there a mass exodus from NYC yes I’m one of them bought a new construction 1.5 hours away are the prices reflecting the mass exodus sadly no or maybe not yet..I had a similar idea as your wife figured let me buy a condo in UWS use it for Airbnb and on days I work late have somewhere to crash near by but I’m just seeing modest discounts on prices in certain areas nothing to get excited about...

If the seller won't play ball, I will then need to decide whether or not this is still a good investment. 

Perhaps there is a play in which you can function as a service provider (NOT a property manager) and pass the management activities through a property manager that you know/like/trust. 

Have you played around with it before?

IMO I think I should be trying to get pre-approved now while my ‘18 and ‘19 W2s are still in play but at the same time what are they going to say when I can’t show them any paystubs after March of this year?

There is concern around market volatility, but cash flowing assets are the safest play in town right now. 

While flipping is always a great play, Philly has an emerging rental market with an average $1000/month rent cash flow.

I've learned that playing SLOWLY is totally fine.

Both of these factors plays a role in my thinking hey maybe they would be to sell if I found a lender that can close fast and pay cash.