For a trailer that old, as noted above, I would pull the wheels and hubs, check the brake components and repack the wheel bearings replacing the inner grease seal...then reassemble and adjust the brakes. If you are not comfortable doing that job yourself I would hire it done. Also check the DOT codes on the tires for the age of the tires. You will get various opinions on this but they should be replaced around 5 or so years from MGF date.
Setting up the brake controller: You really should have the brake controller manual. If you pull the emergency breakaway pin that should apply full battery voltage to the brakes. However, with the pin pulled, just because the trailer resists movement might tell you that the breakaway switch is working but it is hard to tell how many wheel brakes are actually working without lifting the wheels and try turning them one at a time by hand. Also, pulling the breakaway pin won't tell you if your brake controller is working at all or is set up properly. If you pull the breakaway pin don't leave it out a long time as that will run the battery down fast and can overheat the magnets.
You will get a lot of opinions on how to set up the break controller...The best one is the one in the controller manual!
I have seen lots of posts that say check the breaks on a gravel road. However, I have never seen that in a brake controller manual. Most manuals say to set the max voltage manually at or about 6 volts to start with. Then drive 25 MPH on a dry paved road. Apply full breaking manually (by hand) by activating the break controller bar or switch. The trailer tires should not skid. Increase the voltage to the max or until the tires just skid then back off a couple of volts. You want the brakes to come close to locking up but not lock and skid the tires. That will give you your best stopping distance. This is suppose to be done with the trailer loaded. If you do it unloaded you can increase the voltage at the controller on departure with the trailer loaded. Just get it close to a lockup when applying full voltage manually. Some controllers have an A and B switch for lead and lag. There is no right way to set that, just set it as you like it. Some find the lead setting gives a jerky stop in town but like the lead setting on the highway and will switch back and forth...either is fine.
I have set up around 15 or 20 controllers for friends and 3 of my own. All were done by the controller manual instructions as I wrote above.