I've seen a few posts on moving a feral, but most of the situations are slightly different from mine. I have been feeding a feral male with an infected eye for about 3 years now. He may be 4 or 5 years old but hard to tell. I trapped him initially and had him fixed and vaccinated and then once again to deal with the eye (hard to heal without constant Rx). When I infrequently try to pet him, he shies but does not hiss. He will come in the house frequently when I prepare his food but darts out as I approach the door. He can still be aggressive with other cats. Due to my feeding him usually twice a day he's gotten comfortable, a little chunky, and has taken to often sleeping on my front porch (bed heater included). He often is home when I return from work. There are many nights when he is not on my porch so he must have another safe spot somewhere (or other cat to sleep with).
I'll possibly be moving in a year to a similar neighborhood, maybe even quieter, in a town 5 hours away. I would have to trap him, which is difficult. I do have an older neighbor that used to also feed him, but don't know how long he will be next door. I'm not sure which is worse - not knowing how he is faring if he's left, or risk him running away or getting hurt. Any advice would be appreciated.