I'd do both: use a fan while they start, just like you planned. 8 weeks ahead of your planting date is plenty. could do 10 for peppers if they are in bigger containers.
Then when I planted them out, a Wall-o'
water or a cut off milk jug to protect them for a few days.
Tomatoes get planted with more of their stem below the soil. They will put out more
roots and less to blow around when you take the top off.
Plant after your last frost date if using the milk jugs, can go as much as a month earlier with the Wall o'waters. But if you use the WoW you need to make sure they come off before a the first hot day or you could cook your toms and peppers.
When I use milk jugs I drive a stick through the spout into the ground to keep them from blowing away.
It's easiest to set up the
trellis, stages or cages or whatever you'll use to support your toms when you transplant. And mulch.
Everything you picked to start with is great, but they are all going to take more than 2 months to harvest. You will have room between plants in the first month to add a few quick growing greens, like baby lettuce, baby chard and arugula. Radishes take a lot of regular water, but nothing's faster to the table.
Feed the enthusiasm with a fast harvest. If you don't put something in the ground you want, the weeds will fill that niche, so you might as well use it. You can also treat yourself to a 6-pack of zinnias or cosmos for fresh flowers. Or start seeds, they are really easy. Calendula is a fast flower too. Dill and basil are easy, do double duty in the vase and the table.
If you can, find a beater folding chair or a stump or something to set in your plot so you can observe and enjoy your time there. Re-read Square Foot
Gardening, which was motivated by Mel Bartholomew's observations of people burning out in their community plots, while you are sitting on your own patch of dirt. Talk to the old-timers and count
bees. The more pleasant your time there is, the more time you will spend there learning. You have a good plan for a great start.
