Where I am living, our climate is similar to east coast US up near Washington D.C., but very rainy. Even cherry tomatoes have to be in a greenhouse or they will split or just rot without ripening. We are lacking in sunshine in this locality, but if we just moved about 20 miles north of here, we'd have a climate closer to Oregon's past the coastal ranges, but no lack of water. The chillies I attempt to grow yearly would probably do much better there despite an earlier frost. My impression is they really need the sunshine.

Nonetheless, some varieties of chillies have shown up locally that produce fruit more quickly than New Mexico varieties under our conditions. Local heirloom plants have value for that reason. Climate change will alter the mix of plants that will grow well, but the local heirlooms are probably the safest bet for the time.

I feel your pain on trying to grow a nice big tomato. Living in North Florida we have 2 short seasons. I purchase seed and plants from the locale farm store, not a national chain. The mail order seed company I use is Johnneys. Maine has one very short season so stuff for Maine gives me my best chance for a nice yield. Tomatos will not set fruit once the night temps are above 70F if the temp drops below 50F the fruit on the plants will taste like s#@t. For fall tomato plants I take cutting in late May and grow them in pots in the shade planting them in the ground around the first of october and with luck last until end of November. Deteriment(sp) tomato plants will ripen in a shorter time frame than indeteriment(sp) plants as a general rule.

The nice thing about indeterminate varieties (think leggy, climbing tomatoes vs. squat bushy ones) is that they'll produce a harvest over a longer period - so if you're feeding just yourself or a few and can't deal with a larger all-at-once harvest, then indeterminate makes some sense. If you've got a plan in place for preservation and can manage things ripening all at once, then go for determinate.

Baker Creek Heirlooms sells a radish they call an 18 Jours (18 Day) - I didn't have as much luck with them germinating (we had weird weather) as I've had with french breakfast radishes, but I think they're probably pretty good in general.

I can't refrain from praising the multi-headed broccoli (italian in origin maybe, mine are just grown from sprouting broccoli seeds) - the leaves are the most tender, wonderful greens and they're ready early, long before the plant starts to set flowers (or heads as the case may be) - so that might be an option too - because you'll get a long harvest off a relatively fast growing plant. Mine were all volunteers, an entire bed of them, from one over-summered plant from last year that I hardly watered. I'll take seed off that same plant again this summer (it will have crossed with the new volunteer crop) and maybe I'll get something really well adapted to winter/spring here (though it seems it's already doing pretty well).

We always have issues with short growing seasons in Colorado. I've done a little with season extenders and a little with getting local heritage varieties from neighbors, but I'd like to do more. There are lots of seed banks that have popped up in the last few years, but so far I haven't found any local varieties in them. What I have found have been directly from neighbors or family friends I knew in the area. Hopefully that situation will improve a bit as the seed banks mature.