Does it have curb appeal (nice flowers / landscaping, mulched flower beds, etc), Are the amenities like screens and fences clean and looking good - no mold, rust, etc?  

The tree needed to be cut down or all the flowers removed she told me. 

Fourth, add a few decorative touches to make the home more appealing: Place a flower pot full of marigolds or brightly colored welcome mat by the front door; Set a colorful bowl of fruit on the kitchen counter; Install some decorative shelving on bathroom wall; Paint one of the walls in the living or family room an accent color that harmonizes with the rest of the room.Fifth, learn to live with and accept what that renter does with YOUR house.

Nothing major - a fun-colored pot, dish towels, a bowl of colorful fruit and flowers in the kitchen; a shower curtain and towels in the bathroom; etc.

And from there it's going to be 2 years (of birthday and xmas cards, of semi-annual "just checking in, how's the house going?"

I just visited Maui for the first time to celebrate my birthday in February so seeing your post made me smile :-)I would also suggest that you have a few trusted RE professionals wherever you're investing so that you don't have that fear and less stress.  

He even had flower planting on one bill.

ie, do they want a stump dug out or a little flower bed cleared or?

Hi Marisa,Worst case scenario drop $300 to $500 on a new (more quiet) A/C and say happy birthday to the upstairs owner.You'll need to know the amp draw and plug type of the old unit and its cooling capacity.

Wouldn't it be a radically wild concept to reach out with a monthly newsletter, birthday greeting graphic, holiday text or email, or some other POSITIVE feedback during the life cycle of their residency with you - other than "your rent is late"?