165 is going to continue cooking the brisket, so you definitely want to pull well before probe tender.
I also wonder if the convection of the smoker will impact how the hot hold goes. Even wrapped in foil or plastic wrap the air flow could make a difference in how it continues to cook.
What is your reason for holding at 165?
I agree 100% and would have to say pull it somewhere between 185 - 190 in the original poster's scenario, but I too am curious about the reason for holding at 165, as you really are risking over cooking and your brisket shredding when you go to slice it.
Personally, I have been experimenting lately to dial my process in with a 12+ hour heated hold in a warmer set to 140. I don't use the Goldee's method though, I use the foil boat. Originally I was waiting to boat until the thickest part of the flat was 180 (the part of the flat that is overlapped by the point), and pull it when the temp in the thickest part of the flat was 195. But that part takes the longest to come up to temp because the heat in my offset comes from the top down, and by that time the point would be 205 or higher and it would just fall apart when slicing. I noticed that the point and the flat would even out after boating so I started boating when the point hit 175 or so, and pulling the brisket between 192 - 195 in both the point and the thickest part the flat. That made a major difference, but I still feel like the point and the flat in the center of the brisket right under the point were coming out just a little over done. Not shredding but a little "grainy" as they say. My next attempt will be continue boating when the point hits 175 and pull the brisket at exactly 190 in the point and in the flat, but not temping the part of the flat that is overlapped by the point if that makes sense, ignoring that part and probing the thickest part of the flat before the point starts to overlap it. We'll see how that goes this coming weekend. If I feel the point and the overlapped middle of the brisket are still a little over then next weekend I'll drop my finishing temp to 187-188 and see how that does and keep lowering it until I get it dialed in where the point and the center of the brisket slice exactly how I want them. Also, when I pull the brisket, I take it out of the foil boat and wrap it in butcher paper immediately, pouring some of the juice from the boat on the paper and on top of the brisket. The reason I do that is so the brisket is not exposed during the cool down, or the rest. Some will say that will ruin the crunchy bark which is the reason for the foil boat, but that is not MY reason for the foil boat. I like the boat because it tends to let the flat catch up with the point and evens them out. I don't care about crunchy bark personally.
Is the reason for holding at 165 a perceived food safety issue or something like that? If so, I'll say this. I spoke to a food safety expert about this one time. He was a Serve Safe instructor who taught Food Manger and Food Handler courses for people in the restaurant industry. He told me that the guidance is that food hot held at 135 degrees is good for 8 hours, while food hot held at 140 or above is good indefinitely, BUT he said that is really meant for food held in the open in a hotel pan in a buffet type setting, like a pan of pulled pork or mac n cheese etc. You must constantly temp it to make sure the food doesn't drop below 135/140 depending on how long it will be held, ie... over or under 8 hours, and in his opinion it's really just better to stick to 140 either way.
He said something like a brisket being hot held in a holding cabinet is a totally different thing, because it's not exposed. His explanation was that if you cook a brisket to 185 - 210 or whatever your finishing temp is, and then you immediately wrap it as soon as you pull it out of the smoker, letting it rest down in temp to no lower than 140 before placing in a 140 degree warmer is not a problem. This (as he said) is not a problem because any bacteria inside or on the surface of the brisket would be dead when you pull the brisket out of the smoker, and the exterior of the brisket would still be way over 140 when you wrap it, meaning any bacteria that landed on it while moving it to your wrapping table would be killed instantly as would any bacteria that was on your foil or butcher paper once it makes contacts with the 140+ degree surface of the brisket, and the wrap acts as a barrier preventing any new bacteria from landing on the surface, especially if the wrap is foil or oil soaked butcher paper. Now this again is his words not mine but they made a lot of sense and stuck with me.... He said once the brisket is placed in the warmer, you would have to have some kind of space alien genetically modified super bacteria that could get inside the sealed warmer, survive the 140 or more degree temperature inside the warmer, and then somehow penetrate the wrap to get to the brisket, and survive the 140 degree or higher surface temperature. Long story short, not going to happen. He told me under this scenario even if the internal temperature of the brisket dropped below 140 during the hold, it would be fine, because there is no way bacteria can get to the brisket. This is pretty much why these restaurants hold at exactly 140 and you don't hear about them having problems with anyone getting sick. BUT the important thing here is you HAVE TO WRAP THE BRISKET IMMEDIATELY when you pull it. If you let it cool to 140 while it is unwrapped and exposed to the air then all of that is out the window and it may not be safe if there is a potential that the brisket drops below 140inetrnal temp during the heated hold. Even with the Goldee's method, they are wrapping it in foil with tallow immediately when they pull it, and THEN letting it rest down before they put in the 140 degree warmer.
I know that was long, but hopefully it made sense and was helpful. Again this info isn't from me, it came form a Serve Safe instructor who taught food safety classes to the restaurant industry for a living.