Use the roadway water if it's not too polluted.
Is there a lot of trafic?
Swales, i would make them at least 40 cm wide so there is not problem to walk in the trench.
Depth is good, but if you can go deeper, go for it.
Just make sure you don't bring up too much dead subsoil on top of swale mound.
Make the swales when the conditions for growing are there for you in your climate.
Example, making swales in late fall for me is not optimal beacause i don't have any growth cuz of cold.
I could just plant trees as i have quite good soil but anyway there is optimal to have covered soil, living plant or mulch.
If there is
enough mulch (10+cm) for the whole area of swales i would dig them in fall, if no mulch i wait for spring when i can seed swales like crazy and have them green in no time.
Rain, moisture is probalby you main factor, then temperature.
Wait for ideal temperatures and water factor if you don't have enough mulch, dig swales and seed like crazy with all types of pioneer species (clovers, alfalfa, vetch, radishes,
native deep rooted plants and other hervaceous plants).
Also plant some pioneer bushes and trees.
You can plant some hardy productive species such as fig, mulberry, cornelian cherry and others.
Wait for one year and then plant majority of productive trees.
Go for the complete greenery on you swales.
Look around your area for some species that you can get a lot from nature and plant them there.
You can always cut them as mulch when you introduce fruit trees, or if they get in a way later.