Hi,
Welcome to the forum.
In Zone5/6, you should perhaps consider growing the fig trees in pots. And protecting them in a garage for the winter.
There is a lot of reading on the forum, especially search for word SIPS, and pots .
Going through cuttings takes a bit of time. I would recommend to lurk at nurseries (locally and www ) to see what you can find.
You could buy a small tree for 15$/20$, and she would fruit sooner probably.
At the same time, you could start other cuttings for a long term plan.
I'm sure your Madame wants some ten fig trees and not only one ( at this point, you can still pretend that you thought she would want so ) ...
For tomatoes, you can even ground layer them. Just let a branch touch ground and it will make roots.
The only drawback is that the new plant will fruit later... How do I know ... Damn vole ! One vole cut one of my tomato plants at the base. That plant was just so strong, that I just buried it deeper and it made its life into fruiting ... but later than the other undisturbed plants and that plant was not as strong afterwards.