If you're smoking multiple meats of different weights/sizes or species, there are a few options. If you only have one probe, you can wait for an hour or so and probe the smaller piece, or which ever one you think may reach finished temp sooner, then move it to the next one in line to be done. Note that with vertical smokers the upper and lower grate temps are rarely the same...one is almost always at least 10* or so hotter, and this depends on several factors such as water in pan or dry water pan, dry with thermal mass such as pea-gravel or sand with foil on top...there are multiples of configurations that can change grate temp variances.
With multiple meat probes there's less guess-work involved. Having one probe for each type of meat you're smoking would be a nice approach, but sometimes is not practical. You can fit 3, possibly 4 probe cables through the silicone grommet on the
WSM, depending on cable diameter, probe diameter, and in which order you feed them through the grommet. I have run 2 pit probes (1 per grate) and 1-2 meat probes in my
WSM 18, but I feed the pit probe cables first, as they have a larger diameter probe tip...then I can feed a couple meat probes, if desired. I always feed the larger assemblies through the grommet first...you can fit them more easily, and then still have room for a couple more smaller ones.
That said, if invested dollars is not a major factor, and as you stated cooking 2 meats at a time, then 2 meat probes would be my minimum. I have 2 pit temp probes, 3 wired meat probes, 1 wireless meat probe, several long-stem analog pit temp thermometers, 5 analog pocket meat thermometers and 1 instant-read digital pocket meat thermometer. But, I have been known to run 3+ cookers simultaneously with several varieties of meats...not to mention potatoes and at times multiple veggies and additional side dishes. I can use any of my digital probes for pit temp monitoring when cooking low & slow, so I have my bases covered pretty well. Some day when I grow up I want to make complete meals all prepared in outdoor cookers, including dessert...LOL!!! Anyway, get 2 meat probes...you'll be glad you did. If you wait on the 2nd meat probe, for whatever reason, you'll know soon enough if you want it or not...it's just one of many stepping stones along your path of smoking meats...uh, did I just say that? I meant to say smoking FOOD...if you're willing to step out of your comfort zone just a little now and then, you'll realize that smoking (and eating) meat is just the beginning.
Enjoy your new smoker (and soon-to-be addiction)!!!
My apologies...I just glanced at your Roll Call thread...lucky hubby!!! BTW, if you're buying this for him, I assume you're willing and able to eat smoked goodies, even if they're not great at first. Everything gets better with time and practice. Send him here for tips if he's unsure of something. There are tons of beginners here who have asked questions in the past...if a search (advanced search) doesn't turn up a similar situation which answers his question, then it would be appropriate to fire away with a new question.
Eric