Double closings are no longer allowed in the state of NJ so I've been told by one or two title companies that operate and do a lot of transactions in Northern New Jersey.

Every single transaction will be recorded and information will be easily available.

The combined transactional costs alone between the purchase and sale are going to be north of 10% of the transaction value.

Seasoning period is an industry term for the waiting period between your last transaction closing or funding and your next one closing or funding. 

I never really know ahead of time which lender might be open to that before putting the full credit package in front of them, and many of them 'in theory' offer it, it's just a matter of exposing the potential transaction to enough credit unions and banks that a few "swipe left," a few "swipe right," and looking at the terms offered by those that swiped right.

Hopefully, it was based on their ability to successfully execute a transaction, and not just because they were cheaper than everyone else.  

It is very complicated; like a snowflake, each transaction is different.How do you decide risk vs. reward here?

If I cancel an escrow, inspection fees or other costs associated with that failed transaction go in here.

I think where you will be questioned the most is on the new purchase transaction since you have owned your current home for under 12 months.

That would be a prohibited transaction and self-dealing and would cause you to incur massive penalties, blowing up your IRA.