Hey Brock. I just gave up cigars myself for vaping about a month ago. Don't take my word as gospel since I'll still pretty new to this, but I think you'll have tough time finding a realistic cigar taste. I was smoking La Gloria Cubanas maduro for years and I haven't encountered anything resembling that. Although I didn't inhale, I'm certain I was getting a lot of nicotine into my system, especially on 3-4 (small) cigars a day.
Regardless, ecigs do have a wide range of flavors. Many are really tasty. So, you're going to exchange one type of great flavor for another. Since you mentioned cigars and lozenges, you have a nicotine need to satisfy like me. I still have the ten cigars left that I was going to use to help me wean myself off, as well as 2/3 box of Nicorette. I haven't restrained myself, I just don't have any desire now that I'm vaping.
My advice is to move slowly and do research on the hardware. The options are dizzying.
Good luck.