I've only been smoking cigars on a regular basis for about 2.5 years now. When I started enjoying cigars regularly, I would pretty much smoke a cigar a night, and maybe two on Saturday and Sunday if I had the time. If you check my profile, you'll see that I've smoked quite a few cigars in the short time I've been into this passion.
I've certainly found many cigars that have become a part of my rotation. Some of them have come and gone as I've found new favorites to replace old ones, and others have stayed in my rotation. While I continue to smoke my favorite cigars, I still try new smokes as often as I can. For me that is part of the fun in the cigar experience.
Like you said, there are thousands of cigars out there, you'll never find that gem of a cigar out there if you are not experimenting with the cigars you have not yet tried, and the new stuff that is continually being churned out. Can you smoke them all? God...I hope not. My advice is to check with your local tobacoonist, try the Newbie Sampler if you are so inclined, and to just wander the humidor and select cigars that appeal to you. In no time at all you will see which way your palate will lean, and then you can move off in that direction.
Good luck and enjoy the ride.