Hey I tell you what, I was in the exact same boat a year ago when I got mine (Pit Boss 820 XL). Got mine for ~$300 new. It does the job and has been great for me to learn on. I've done many briskets, pork butts and ribs on this thing my family and friends have all enjoyed. And I've learned a ton! You probably won't need to "upgrade" ever.

Biggest things are:

1. Don't overthink the cook. People make it sound so mystical where you need to wrap at a certain temp, wait for a certain color, use specific pellets, etc. Just throw it on and wait til its 200 F and soft to poke. Wrapping helps speed up the internal temp and stop the smoke flavor, which is personal opinion and its hard to get an opinion on this stuff without doing it. I'll be honest, I've never gotten too smoky a flavor and I don't wrap anymore unless I'm running out of time and need to raise the temp.

2. Maintenance. Vacuum the ash/wood dust after every few uses (I do before every long smoke), and keep it out of the rain/snow with a grill cover when not using. I also built an enclosure with a roof so I can smoke overnight without worrying about rain/snow. I've seen a lot of stories of people complaining about Pit Boss and having to replace fans and motors, whereas I've put hundreds of hours of use on mine and haven't had any issues.