When I've started them outside, even in little slits in a covering sheet, I've always had nasty surprises: damping off, insect attack or late frost, and had to start over, very late, which means I lose them, in their bearing prime, to early frost in September.
So I start them indoors now, and transplanting hasn't been a problem. I use peat plugs, not pots - cheaper and neater. I put those in punctured pudding cups in the hatching shelf,
- until it's time to transfer to a pot of earth, with minimal disturbance to the roots. Most of them are in the nursery tent now, thriving.
(That was taken a month ago, before the tomatoes outgrew it. )