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If you liked your pit boss, take a look at the Louisiana smoker. It is from Dansons, the same guys who own pit boss. I really like their side burn system, which is much like the system used in a Yoder. (MUCH better than pit boss burn system, which is the same burn system as Traeger).
Support has always been great. Their sear unit makes it work great as a grill.
We use the Louisiana as our "everyday" unit at home.
I'm loving my Camp Chef Smokepro STX more and more with each use. That's about half your budget so the Woodwind with sear box might be up your alley. I had Pitboss for about 3 days until i returned it to get the CC. I had 100+ temp swings on the PitBoss and i just couldnt accept it.
I have the Daniel Boone model from Green Mountain Grills. Very well built unit. I added a product called grill grates and am able to produce great sear action utilizing the grill (see attached).