I hear you there about the short season. I never even try to put tomatoes out till June 10-15 and just hope I can pick a few before the Sept frosts hit. Last year though we got lucky and didn't get frost till well into Oct, so I still have blanched tomatoes in the freezer!
Last year was SO frustrating! The previous year, we had a car in the driveway that wasn't running, so I used it as a greenhouse until we could plant out. It worked REALLY well and we had beautiful plants. Decided to try the same thing last year with our tomatoes, however, the forecasters said it would be in the 40s and instead it dropped into the teens a couple nights. Bye, Bye tomatoes, even though they were in the car! We would have taken them inside, had we not been given false information.
After that happened twice, I had to buy bigger plants, but they never amounted to anything since we couldn't plant until July. Hoped for a long autumn, but got frost in early September.
This year, I already put in snow peas, spinach, radishes/carrots and bunching onion seeds (from some old seed I found in the garage) and if the don't come up then I will replant those spots later. I bought some baby bok choy to try out this year. I will do zucchinni and lettuce as well. I am doing Kentucky Wonder pole beans too but they don't go in till June either.
I think my tomatoes and peppers will mostly go in containers this year. DH had good luck with his peppers in 5 gal buckets last year.
We are in drought this year, so overall our weather is warmer. We nearly reach 80 one day, then drop way below freezing at night unexpectedly. It was in the lower 20s when DH got up this morning. If I don't get my cool weather crops in now, we won't have any, when temps start sky-rocketing during the day. We've planted all sorts of greens and so far they are doing pretty well under plastic coverings. Don't have enough milk jugs however! Can't get them from recycling here, because of ordinances.
Found some small clear plastic bowls really cheap out of desperation and used a few of them on my remaining baby bok choy, however, they are so shallow, that will only work for a week or two. Found a cracked plastic bins at a thrift store the other day. They were charging too much IMO, but hopefully I'll be able to keep them for a few years. Some of my bok choy and Swiss chard has been in for a couple weeks now and is really happy under milk jugs. Got my broccoli, purple sprouting broccoli, lettuce plants and onion starts planted several days ago, and they are doing well. Put in my mustard, kale and more baby bok choy Thursday and they seem to be doing well. The arugula and spinach-mustard seed I planted a couple of weeks back is beginning to sprout. The onion sets I planted for green onions shouldn't be far behind them. I really need to divide my shallots, but haven't had the time. No sign of the early planting of beets, lettuce, kale, leeks, rat-tail radish and Swiss chard seed I put in at the same time, but at least some of them should be popping up shortly. Think I put in some mizuna and possibly bok choy seed at the same time, but didn't have any plastic knives to write on at that moment, so now I can't remember what I planted in a couple spots. I'll keep watering it and enjoy whatever might come up.
My old house had a huge garden, but this new house is limited on yard space so I only plant a little for fresh salads/stirfrys and don't count on anything left for the freezer or to can.