Kert you must be fast...takes me about 40 minutes just to clean my airless...VBG
the lone....first off what kind of wood are you planning to paint? Is it new wood or has it weathered?
If it is new fresh lumber then you should prep the wood to accept the paint. The milling process these days is so high speed that the lumber gets a glaze and paint can't penetrate. There are clear products you can spray on that break up the glaze then paint.
If you are using an airless sprayer I would backroll. That is the way my wife and I paint our fence and house...well it is until ladders over 6 feet are involved then I do both.
There are some who can spray only but they either have lots of experience...or none....
you can cover a lot area with the sprayer and back rolling is as quick as you can roll.
Also be aware that even though it is airless the overspray will travel a long way and you must cover anything and everything, beside, around, under, before, past, over and generally within 20 feet....especially new cars....this is asumingno wind...if windy all bets are off.
I would use a modified solid stain. You can clean up with water but the base is like an oil based stain. I've used Flood stains and have had good results.
Be aware of wind, air temps, substrate temps....you may be shooting at 4 in the morning...
Good luck with it....BTW I bought a Wagner that has a one gallon hopper on it in the early 90's and I still use it. Replaced the gun and the hose is next but it has paid for itself many times over.