Oil usually sticks to oil
Latex always sticks to oil
Latex always sticks to latex
Oil never sticks to latex.
I like latex because you can clean up with water, but that's just my $0.02
I also like vinyl siding
Good tips, though I don't care for vinyl siding.
No paint sticks to peeling paint though, and paint doesn't stick all that well to dirt either. The devil is in the details of prep.
How much of the old paint is peeling off ?
A pressure washers will do a good job of blowing off loose paint, but you will have to wait at least 24 hours to start painting.
Bare wood should be primed and I prefer oil based primer. When you say spray, I assume you mean an airless sprayer. Buildings are no place for typical air spray gun ! Latex is the way to go. You will still have over spray. I like Sherwin-Williams paint, but wait for a sale. They usually have one around labor day.
Do NOT paint in direct sun (unless it is early AM) or extremely hot weather. Just before dark is not good because dew can get to the paint. If you get pushed into late fall, do not paint if the overnight temps are below 50.
I would say that 24 hours in full sun is still nowhere near enough time after pressure washing. I'd recommend at least a week. More on a north facing wall (in the northern hemisphere). Otherwise moisture will still be in the wood, and can lead to poor adhesion and blistering/peeling.
24 hours is enough time if you use a hose-end chemical sprayer and soft wash with TSP, followed up by a hard scrubbing to remove anything loose. This is the gold standard for prep.
Oil based paint works fine even in cold temperatures. I've Kilz (oil based) primed many wood things in my garage in the winter below freezing. But your advice is still sound. You especially do not want latex paint drying at the wet edge as you apply the next stripe, which means avoiding the direct noonday sun in hot weather.
Like you, I too am partial to oil based primer on wood. And latex is your best choice for an exterior top coat nowadays.
Sherwin Williams runs a LOT of sales. It's best to go there and sign up with your email address to get the most discounts. 40% off is not unheard of.