Quoted from Drano:-Airbrushes (Paasche/Badger), siphon or gravity feed? Single or double action? Any other considerations?
I use an Aztek double action airbrush. I have various size paint cups that are ether gravity fed or siphon fed based upon the size. My Aztek has interchangeable tips for different spray patterns.
Quoted from Drano:-Best paints/mediums for the above? Any advice on best way to color match?
Like Tatman, I use water based acrylics. The majority of mine are Americana brand. There are two ways to colormatch and I use both. Primary is using a Pantone Color Guide. Get it off eBay for around $20 or so. Don't pay for the $60-$80 ones, just be patient, the $20 ones come around fairly often. Match your touchup area to a color on the guide, mark it (I write the name of the machine on it) and take it to your local Michael;s or hobby store. The other method is to mix your paints to get the shade you need. I use a 12"x12" piece of glass to mix on and them lay the glass on the playfield to see how closely I have matched the color. During the mixing process, I write down how many drops of what color I have added so that I can repeat it if I need more of the same color. When I have the right color I use Frisket to mask the area to be painted. I use a #11 scalpel blade to cut the Frisket. Scalpel blades are a higher quality steel than Xacto blades and stay sharp longer. If your blade isn't sharp it will pull/stretch the Frisket as it cuts and lift it from the surface. A good likelihood of paint seepage will occur if that happens. After cutting it with the scalpel, I use a nylon decal squeegee to ensure the edges are down.
Quoted from Drano:-Best epoxy wood filler for outhole repair from a color match and workability POV?
No help here since I use Bondo for all repairs. After shaping and sanding I use the Pantone Guide to "match" the color of the surrounding wood and paint it.
For your last two questions, I can't help there as I've not had the occasion to do either of those types of repairs. Hopefully someone that has done those will chime in.
Lastly, I need to give proper credit where it's due. Some of what I learned I got from reading Cliffy's Jumping Jack restoration. I also learned about color matching wood from reading Chris Hutchin's restorations of several machines. I am definitely not, in any way and by any stretch of imagination, in the same category with either of those gentlemen. They both are phenomenal. However, through them I have been inspired and given the confidence to at least try some of these repairs myself. I practiced airbrushing for many hours on cardboard and old playfields that I was either given or had as a result of a swap out.