Annie,
It sounds like you are trying to embrace the CSA model. I have worked for several farms with CSAs and none of them (nor any I am aware of) offered produce to their subscribers year round, but rather for 8 to 9 months of the year with the last box being a big send off full of storage crops.
That being said Several of the farms I worked for where also direct wholesalers to co-ops and grocers and the like - and we did
sell to them year round. During the depths of winter we would rely on selling from our stores from our fall harvest like beets, potatoes, and winter squash as well as leeks and parsnips and the like.
Either way there is a learning curve and there is an unavoidable margin for error. The key is to keep commitments loose and work with customers who are cool with that. Especially when starting out over plant and plant lots of stuff knowing that some will fail and some will get away from you. Make it clear to the customer that you are committed to supplying them with produce, that they will get SOMETHING but also ask them to be realistic and tell them what (and when) you expect to be harvesting. A newsletter that leads the weekly box by 2 to 4 weeks is a huge boon for the customer and a giant pain in the ass for the farmer.
Bolting plants can be tricky. You can't count on planting in succession. Even if you plant out one row one week, and one the next, and another the next a good hot/dry spell will likely leave you harvesting them all over the course of 4 or 5 days. But not always. It's tricky. Again I will stress having a variety and a number of 'fall back' 'crowd pleasing' fillers. In my experience this is generally more salad mix.
You can get hella sneaky with greenhouses. I could regale you with stories about the 9$ bunch of organic carrots which flew off our market tables, but I won't.
The key is to learn your plants. Get a feel for your climate. Then its mostly timing timing timing timing timing timing timing timing timing timing timing timing timing
and what is it they say?
Nothing ventured nothing gained
Best of luck, hope this is useful. I imagine NZ to be pretty similar to the PNW, but have never gotten to visit way down there.