don't have any experience of this yet, but plan on doing the same thing, I'm about 30 miles east of you, so interested to see the responses here. From my short experience of growing peppers here in containers though, I'd say it should work a charm!

I have grown peppers in Earthboxes...

I like to have better control over watering and fertilizing my pepper plants. With the Earthbox, it's more difficult to "stress" the plants. Also, if you follow the instructions, there is a layer of fertilizer between the two planting rows. I configure my Earthboxes with two rows and 4 holes per row for a total of 8 plants.

I believe the recommended configuration tends to overfertilize the plants as they have very dark green, large leaves[and not much fruit].

What I do like about the Earthboxes is that they allow me to germinate [in situ]. After the frostfree date, I simply place the seeds in the holes and let nature take its course. No multi-transplanting and hardening off.

When the seedlings get large enough, I simply transplant to the ground or to the pot.

It's a great germination system for those, like myself, that have over-full garages and homes with not enough space that's required for germination inside....

I live in St Pete and don't know what earth boxes are but I have raised 2 plants in containers for almost 3 yrs now. I also grow in raised beds. This is the first year I've gone for a second harvest, so far my in ground plants are doing ok, but haven't set much fruit, seems the dry summer wasn't the best thing for the plants.

I have found that if you keep the plants protected during the few cold weeks we have (wind block) they come back strong in february.

I have grown Hungarian Wax, Macho Nacho Japs, Mariachi Japs and bells in fax earth boxes 18 gal size and plant 6 per container. The Bells were cut back this spring and roots pruned and replanted. I got bells before our hot period and now that the weather is cooling off at night and under 90 in the day time, I have more pepers than I can use. I give away my surplus. If we have a freeze then I will cut them back and prune roots and replant 2 each to a 5 gal bucket for then next season. If no freeze I will cut back to about 1/3 and start watering in mid Feb using blue stuff each week.

I saw no difference in the growth rate or production of those pepper plants I grew in my Earth Box and those I grew in 3 gal. pots.
-Junkmanme-