A fellow 5b pepper grower, so I thought I’d weigh in. With some advanced planning, you can grow just about any pepper variety. With an early enough start, all the C. Chinense are doable. I’ve grown 7 Pots (4+ ft.), Habs., Bhuts, Nagas, Scotch Bonnets, the Trinidads, etc. (all the usual suspects). The key is to get an early start on the seeds for my target plant out date around Memorial Day. Annums will do fine as well. Easy to start and grow with good yields. You mentioned Jalapenos, Cayennes, and Serranos (one of my all around favorites). You may want to consider Fresnos and the Numex varieties (i.e. Anaheim, Big Jim and Joe E. Parker) and the Asian types (Thai hots) as well. I also grow a fair number of ornamental peppers (Royal Black is a beautiful plant) that I grow in pots and place out on the deck. They are easier to maintain all season than flowers and have a high wife acceptance factor. The C. Baccatums I grow (Aji Limon, Lemon Drop, Inca Red Drop, Aji Orange, Brazilian Starfish) are big plants (4+ ft.) with loads of pods. I am scaling back on the number of these I plant because they are so prolific.
Keep in mind that if one only buys plants from the big box centers or garden centers (at least in my area) you are limiting yourself on the varieties of peppers (especially the C. Chinense) that can be grown. It was this limited availability issue that got me into growing peppers from seed in the first place.
The varieties that I’ve not been successful with are the C. Pubscens (roccoto) that never did ripen the year that I grew them and last year’s C. Frutescen (Bradley Bahamian) that did the same. I’m trying a couple of different types of the latter this year to see if I can obtain better results. I am not into over wintering, but reports that I’ve read is that the roccoto would be a better producer in year two.
The major factor on the success of the season we here in the North are faced with are weather variables. Cold springs, early frost or cold temps. in the fall all have the effect of shortening the growing season. We can do some things to extend the season (hot house covers) but my pepper garden is to large to cost effectively pursue such devices. “It is what it is” I guess when it comes to Mother Nature. Last two years have been great, early starts with no frost and the season extending well into October. In 2009 was the opposite, over 50% of the crop never ripening!
Good luck on your upcoming season!! That are a number of very knowledgeable people on THP, lots of good information can be obtained from perusing the numerous message boards.
Note after re-reading your last post: Do not worry about Hab. yield in year two. Assuming that you’ve got good plants and a reasonably growing environment, you will have more peppers than you know what to do with.