Fun times ahead!
I used to make quite a few tomato crosses but my eyesight isn’t what it use to be. I never found it really easy because I have largish, clumsy hands. Combined with poorer eyesight I now ruin at least half my attempts. Luckily I’m a stubborn old crock and just keep going until I succeed.
I have lots of crosses I want to do this season. For most, I’ll collect pollen from all the potential dads and mix it before applying it to the potential mums. Only a few of the crosses are between very specific parents.

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Great idea to use potato leaf mothers. Makes culling the non-crosses a piece of cake.

This sounds like a wonderful project! Good luck with the crossing/hand pollinating, I had all kinds of plans of crossing some heirlooms i like last season, but they withered. Too close to the black walnut tree and the few fruit they did set tasted sour and bad so i never tried to actually cross them in the end