I like your approach, I used to use maps and a spreadsheet to plan things out. With my new growing system I am faced with a new problem, I am using an un-bordered square foot approach and have plants in 3 stages going all the time (just planted seedlings, re-potted plants up to about a 6" pot, and plants maturing in the garden for harvest). As a result I am constantly rotating things. I seldom leave any space unplanted for a week Normally, I harvest, ammend, and replant on the same day. I have 4 growing station shelves, each has 4 starter trays, no more than 36 seedlings per tray. 6 of the starter trays are the final home for indoor tomatoes, cucumbers, laurel bushes, and herbs. The laurel bushes are now about 4 years old, but every year I pull them up, trim them back and repot them. The tomatoes only last about 18 months before they quit producing. The biggest problem with the tomatoes is finding the proper seeds for replacement plants. This is the first year that I have been able to get fruit off indoor cucumbers but I don't know how long the plants will hold up....
I have learned the hard way that some plants are very sensitive to things like nightly lows, or mid-day highs. For example; if I put okra plants outside before the end of May the cool nights here will really set them back. Spinach on the other hand doesn't like the mid-summer heat... We have so many insects that love my squash plants that I can usually only make a few harvests before the plants fail. Last year I did staggered planting of nearly mature plants (grown indoors), by moving the plants around I was able to get continuous harvests until frost killed the plants. I would love to figure out a variety that didn't need a pollinator that I could grow long term in one of the growing stations.
This year I am trying to add a pair of elevated outdoor growing stations (shelves) where I can bring plants in 6" pots to harvest. Each shelf should be able to hold about 18 pots with lettuce and such. With the growing stations, watering becomes an issue, if I start traveling again it can be a week or so before I can check in on the plants, they just can deal with that in the summer....
My San Marzano Tomatoes (for canning) are about a foot high, I hope to have their beds ready by the first weekend in May, until then they are in starter trays sitting on my battery box in the greenhouse (enclosed walk out basement). In the past I have moved them outside too early and they just floundered.
My outdoor garden is very small(postage stamp), less than 300 sq-feet of growing space (not counting walkways). Much of my garden is in raised beds, containers, or tubs (storage containers with broken lids). This year I have 3 tubs and one raised bed with potatoes (these are all the high end plants, you know the ones that just sprout while waiting to be cooked).
Every gardener has unique objectives, my objective is that I want to have a steady supply of salad makings, a few crops for cooking and canning, and a few experimental plants for variety. I don't want to waste anything, so getting consistent small harvests are the key. My goal is to have 9+ months of harvestable growing season every year. This is a relative ambitus goal as the typical time between the last frost and the first frost is 7 months. This means that I need to be able to grow things for at least an extra month on each end of the growing season when frost is an issue...