On paper it makes sense but I would be curious if anyone with more experience on this subject matter has an opinion.thanks!!!!

$100K plus the $250K exclusion then anything over $350K is subject to capital gains. 

It's probably best to start by reading up on some books on the subject as well as networking with others here who have done these types of deals already. 

I'm fine to do 5 year seller financing and allow subject if other terms are met.

Subject-to arrangements are uncommon among lenders.

.- thanks ...try reaching out to the local small to mid size  credit unions and banks in NJ ...contact the bank you  have your checking / savings with ...contact the lender that services your 1st mortgage for options .....regarding deprication - are you asking about the depriciation on the  primary home ( subject property ) being added in or  for the depriation from another property ?

The appraisals that consisting come in close to what a property actually sells for are where the subject is an income producing  property being run on a consistently and providing consistent cash flow.  

So much so that you might consider breaking it up into separate posts on each subject.

I've been reading a lot of books on this subject lately.

@Dylan Speer sell it, come up with the negative money balance, write the loss of on your taxes and move on with your life.You can sell it "subject to" to someone looking for a home with no money down and save on Agent commissions?