Being a developer and investor in Boston, the only way a property is going to be a "good deal" is if there's a value-add play. 

I think the best way to continue valuation is to add revenue and expenses from the house as if it were a rental and then add in all expenses, that way you get a full P&L picture and it negates the weird game the seller's trying to play with the expenses.

But another part of me realizes how nice it would be to have 35k extra dollars to play with.

@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.

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.