I realise it’s conceivable this may vary based on local law - but is anyone familiar with a prospective tenant being held liable for any amount based on an email assurance that lease terms would be acceptable/signed, then declining to sign a lease?  

You cannot 1031 into properties you already own or to pay down a  loan on a property you own.You're lender is probably giving you a partial release when you sell in exchange for a certain % of the net proceeds from the sale of the one unit.While it is conceivable that you could do a 1031 on this sale I think you need to look closely at the issue of intent.  1031 is only available for properties you have purchased with the intent of holding for productive use. 

If both parties are unrepresented, and you just make the connection and want to charge either or both of them some kind of consulting/admin fee, that would conceivably be allowed...if your broker allows it*, and the if fee is paid to your broker.The customer always pays the broker, and the broker always compensates the agent - you can not be paid directly by the customer as a sales associate.

Yet you still own it and conceivably collecting positive cash flow.  

This allows your direct mail pieces to tell a story and build confidence in the mind of the prospect.If you are serious about growing your business then direct mail is something you want to be serious about implementing as one of the most effective ways to both get your marketing directly in front of your prospects and to scale your business to any size conceivable.

The student loans are probably not too punitive on your borrowing capacity since the minimum payments are pretty modest typically, and the rates aren't too bad.You're going to determine if you can conceivably invest on Long Island and make any money.

It's so disheartening living in a state that has every conceivable industry, tens of thousands of acres of farmland that is blocked from use, and if it were a country could be one of the most wealthy in the world, yet the mismanagement by our state government for decades has cities rushing to file for bankruptcy.

There used to be a saying "As California goes, so goes the nation", with the liberal policies of California, cities/counties filing bankruptcy, prisons releasing thousands of prisoners, hundreds of millions in unfunded public employee union obligations, taxes and fees on every conceivable thing going up.....

They know about strategies that you don't even know to ask about.As others have stated, however, you need to get one who is very familiar with real estate investing, and conceivably also with small business strategies.

Conceivably you could use a reputable turnkey (yes, we're all sick of this term) company, but you'll pay their fat markup (probably 20-30%) and won't get yields above 8-9%.I will say that once your team is in place, the incremental effort on each new deal is dramatically minimized, as would be expected.