Possible short with rear tail light and trailer lights

2003 Tahoe....My rear passenger side tail light went out so I replaced the bulb. That
didn't solve it so I checked fuses inside the cab as well as under the hood. They were
all fine. The other night I hooked up my trailer. At first all was normal but a short time
after i noticed that when I applied the brakes the trailer lights would go out. I went to
check the plug and low and behold my non working tail light was working just fine
again. The brake light issue continued until I was almost home when I noticed the lights
on the trailer weren't going out when I applied the brake. I then checked and of course
tail light was once again gone.

My question: I'm just wondering if there is a area or specific place that a short of this
nature happens rather then having to trouble shoot wiring from front to back. Or maybe
this isn't a short but I would have to think it is. Wondering if theres any feedback out
there that may make my repair process a little easier. Thank You in advance.