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

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.

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

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.

------------------------------------------------------------------------------------Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

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.

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

Financing- build a relationship with a regional banker, don’t shop for interest rates, start small and build history and loyalty they are your team, Cross collateralize, deposit CD/MM or custodial account with bank for loan, give them monthly updates, nail your deal analysis, do stress tests on your deal analysis-cost/interest rate/deal length/ sale price etc. 12.

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