That glowing review, along with their preference for a two-year lease, and their desire to build a deck and fence on their own dime all paint a picture of a responsible tenant, the kind I should comfortable reaching out too with minimal risk of repercussion.Thoughts or suggestions?

Nickels and dimes.

I'm surprised they'd even let you fix the plumbing issue on your dime before closing.  

You have greatly improved those two neighborhoods and earned every dime you made!

awesome write up @Mark Updegraff Some people need to understand that it's not solely about the buildings, its about relationships & who you know.I choose not to work with those that think all agents are a dime a dozen (admittedly many agents are) If someone thinks agents are a dime a dozen they will work with a dime a dozen agent every time.

They feel (and rightfully so) that their profit is no one's business or want to ensure they don't get nickeled and dimed on the next deal.

Each of the 3 things that you ask about is actually its own full area of study.For the Syndication part of what you ask (and I wholeheartedly agree, you should not raise capital from others unless you have a profitable business model that you can execute, don't learn on others dime) I recommend the Real Estate Guys course "Secrets of Successful Syndication" - I have gone many times and it has been invaluable in helping me in my business.  

I can tell you, though, the beauty of his situation is that he did not have to put a dime down on the property. 

If you are changing careers with hardly a dime to your name except for a down payment then that will be tough to find a lender that says yes.

I don't feel like nickel and diming good tenants each year is necessary but I would get another year lease signed by them.