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While a UDS is a wonderful smoker and the cheapest option. I still feel a WSM makes the best first smoker.

I know that the 18" is the one that fits your price range, but if you were to get a 22", you would never NEED another smoker I would bet. It is considerably larger and handles full packer briskets and ribs easier. With Weber's wonderful porcelain coating, they last forever just like the Weber Kettles that everyone is familiar with.

They also break down for easier cleaning and ash removal than a UDS, this also makes it easier to travel with if you decide to take it camping or on a trip.

WSM all the way.
 
I started with a cheap Masterbuilt gas smoker and it's done well for me. Obviously, the temps are easy to dial in and maintain, and it lets you really focus on timing and flavors. Granted, there is a big flavor component missing with the absence of the charcoal, but I've never had complaints either.

I've picked up an OTG recently and can notice a big difference in the flavor already, but I think starting on something so easy to use was a good way to go.
 
While a UDS is a wonderful smoker and the cheapest option. I still feel a WSM makes the best first smoker.

I know that the 18" is the one that fits your price range, but if you were to get a 22", you would never NEED another smoker I would bet. It is considerably larger and handles full packer briskets and ribs easier. With Weber's wonderful porcelain coating, they last forever just like the Weber Kettles that everyone is familiar with.

They also break down for easier cleaning and ash removal than a UDS, this also makes it easier to travel with if you decide to take it camping or on a trip.

WSM all the way.

Yeah, I thought the exact same thing a little over a year ago. Now I have an LSG on order. Don't get me wrong, I love the WSM and I am glad I bought it. But I got into this quickly and decided I want more room and don't want to mess with pulling the top rack to get to the bottom rack.

For someone starting out, I would strongly endorse the WSM, and if you are going to get one, get the 22.5". Just don't be too surprised if after using it for yourself, family, and friends, a bigger smoker starts to appeal to you.
 
I'd add just a regular Weber kettle to your list. It's big enough for a brisket flat/point, chuckie, or a rack of ribs. Depending on how much meat you think you might cook it might be enough. PLUS it's a great grill.

If you need additional capacity I'd go with the WSM. Weber makes good stuff. Just my opinion.
 
Good luck. We want to see some q view soon. I bet a used wsm and building a nice UDS will be about the same price. But it could take awhile to find a used wsm.
 
I enjoyed learning on a charcoal, felt it forced me to understand the process more. So my vote for a first post is the WSM.
 
First Butt!!

Thank you all for your thoughts. I ended up buying a used 26 inch Weber Kettle for $50.
I've been doing hot and fast cooks since I got it, but, this past weekend, I finally got to try it out low and slow.
I used the 'snake method' with 5 briquettes, 3x2. Cooked for 10 hours!
I did have some trouble at the beginning trying to regulate the temp. Nothing a bit more practice can't cure. And, I admit it, I couldn't resist and gave into temptation. I took a peak at about the 6 hour mark.....BIG mistake! Took forever to get the temp right again after that. (note to self- don't peak!!!)
Anyway here's the pron!!! (I didn't do a before)
 

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