In my experience it becomes a small part of your routine.
I don't sleep in my watches, so if I only had a hand winder, I'd wake up, wind it and put it on, it takes, what, 10 seconds?
I've got two pocket watches on stands around the house, they need winding daily, but it's just something I do, like eating breakfast or brushing my teeth.
The only thing with those is that if I go away they stop and need resetting, but if you're talking about a daily wearer watch, you'd have it with you anyway.
With a flieger, the more realistic, the less practical on the whole - I like the style, but settled on a more practically sized Laco Aachen (actually I have two now), which has an automatic movement and is 42mm across.
Laco made some of the original watches, so you're getting that connection, but the Aachen is a more usable (and affordable) option than many of the more 'authentic' fliegers (including their own, higher spec models).
Happy hunting!
M