Home Improvement

My small garage was built in the 40s and has wood siding which was damaged by a recent hail storm. Insurance cut us a settlement check and I decided to challenge myself to repaint the garage myself

The hail mostly damaged the paint, with some small chips in a couple of spots. My plan is to sand the portions that are to be repainted, fill the chips with wood filler and repaint

I'm looking at getting an air compressor (Partly as I'm seeing commentary on it being far easier and faster than rollers, and partly out of buying a tool I might not ever have a decent enough reason to buy in the future that'll be useful to have on hand) and a sprayer to do the bulk of the painting

Given I'm mostly looking to repair some quarter size damage to the paint splottered all over 2 sides of the garage, do I need to sand all of the old paint off before repainting or can I simply paint over the old paint? The old paint is in pretty good shape where the hail didn't sand it away. Looks like its been repainted within the century, possibly even within the last decade, and I'm not changing colors dramatically, just doing a flat "white" over a flat "white" which shouldn't be a very obvious difference after weathering. Basically am I reducing the durability of the paint job if I paint over the existing undamaged matte paint?

Additionally, any other gotchas I should be aware of?

I can provide photos tomorrow of the damage and existing paint if needed