I've probably had two dozen different brands over the years. Briefly started a journal at one point, which I no longer have.
Surprisingly, because it's not supposed to appeal to beginners/infrequent smokers, I found I prefer darker and bold cigars. My go-to is Partagas black label, Partagas 1845 is also very good and a bit more mild.
Don Diego is a very mild cigar that CAN be excellent (and relatively inexpensive)....but IMO tends to be pretty inconsistent (had a number of really good and really bad ones).
Cohiba's are very popular, but I'm not a big fan. Same with Romeo & Juliet, though both are pretty consistent and mild/medium side. Ashton is another example. I've had some good Padron's. Also a few Davidoff's I liked.
Start sampling and find out what you like. I landed on Partagas early on and pretty much stuck with it given I only smoke 4-5 cigars a year. I'm not refined enough to speak to quality, just that for me the big differentiator is mild/medium/bold, and I found I prefer the dark/bold cigars.