I was thinking he may want to start keeping his yard up so the neighbors won't have too but I didn't want to start any trouble.

I would worry more about getting rid of that dang wisteria, stuff is worse than kudzu.

I live next to a guy like that. We call him Wild Bill. His fence is about 4' off the property line on his side. Constantly reminds me all the time. Cuts that 4' of grass every week just to keep reminding me. Recently put up a Chartreuse string from the back corner marker to the front. I thought he was going to put up a new fence but he ended up taking it down after about 6 months. I just try to avoid him, smile and wave.

I say help.
I have actually cut my neighbors yard without asking. They will let the grass and weeds get nearly thigh high all over the yard then they'll cut part. All the neighbors were complaining and talking about them. My feelings were that if they could cut it then they would cut it. So, I did what I would want someone to do for me. I went over while they were at work and cut their grass. They never asked who did it. I cut it 2 more times that summer. Come to find out, they had taken in a foster child, husband lost his job and was working a new one that required overtime and wife is not in good health to cut the grass. None of the other neighbors stepped in to help me, they were too busy talking about the "lazy neighbor". Sometimes you have to look at people thru a different set of glasses.

Where I live, I'm the very first house in the subdivision. The HOA hires people to keep the entrance mowed. Usually, when a new crew shows up, they start cutting a large portion of my side yard, thinking it belongs to the neighborhood. I always ask them to stop because they scalp it with their mower setting.

Next thing you know your neighbor will be taking your wife out for lunch while you are working.

i used to cut my some of my neighbors yard. He had a big tractor type with a belly mower. I knew he couldn't cut around his trees because of the low hanging limbs. I took it up on myself to mow it for him wihtout asking. He never said a word and he would till my garden spot each spring if I asked him too.

As for as taking the wife out to lunch, saves me on the food. LOL

I fooled him I'm not married to the woman that lives here.

Im glad my neighbors are cows, a peach orchard, and 60 acres of uninhabitable rocky Mountain.

Sorry dude, I was just preparing the spot for my ganja strain called Rainbow Diesel Funkadelic Cheddar Harmony.

People where I live do this occasionally. I also send my son over to get my neighbors paper and bring their garbage cans in for them. It's just something that needs doing so some people just do it. I can see where it could turn into a problem if you don't actually know and talk to your neighbors.