I think gifting tenants is a bad idea.  

What the lender required, was that they write a letter saying that the money was a gift and not a loan.  

Hi Matt,Step one might be to get them a new baby gift or two---like a couple of little stuffed toys from Target or Walmart.Drop them at the door in a box like FedEx does with a nice little card of congratulations on the new baby.If that doesn't make YOUR life easier, then wait until the lease runs out.

I might knock on his door with a nice gift- maybe a fruit basket or something, and just say you are introducing yourself to the neighbors and tell him how excited you are to be a part of his beautiful neighborhood.

The neighbors watch my more remote property, (a $50 gift card at Christmas encourages this) and the PM drives by my city properties weekly. 

They get a big tax refund (actually a gift, since they usually get back more than they put in) and squander it on a vacation or booze or drugs or new rims for their over-priced car.

@Matthew Kelley, did you buy the property in question or was it gifted to you? 

He has already given you a gift by charging you under market rent for 20 years (rent control or not), and now you want him to pay you to move out or profit off of his low rent by subletting the place for more money and pocketing the difference?

I was thinking of a gift card for a dinner or maybe a place like Target for supplies in a card or gift basket.

Yes you eventually have to take chance on them, but when they do well, tell them, buy them a $25 gift card to starbucks, take them to lunch.