Hi Scott, you're peppers look really great! You seem to have a great jump on the season.
I too overwintered a plant last year (Lemon Drop). I grow in pots anyway so at the end of the season I just root pruned it (which it really did not seem to mind) and severely pruned down the growth and stuck it in a 1 gallon nursery pot to over winter near my patio window. I am very happy with the results after the replant.
I am definitely going to do this again after this season (albeit with a few more plants, of course
)
My question to you is, how many years can you keep the same plant going? You said a few of your's are on year 3. Have you ever successfully kept one longer, or is it better to start from square one after year 3? Any advice would be much appreciated!