I haven't worked with your particular situation, but you'll probably want to look at where the debris is trapped. A cleaner with a large bag is probably better for leaves and needles, but one with a small filter cartridge may be better for dust and dirt.
However, in your area, screened pool enclosures are common, and if you get an enclosure, then needles won't be an issue.
If not, then having multiple well-placed skimmers with a low-resistance high flow circulation system, coupled with a 2 speed pump that can economically maintain that high flow 24/7 would be something to consider. No vacuum is going to be as easy as removing needles from a skimmer basket with a sock.
Such as system might consist of a 1.5HP 2 speed pump (like a Hayward Super or Super II), a 24" sand filter (up to 20,000 gallons) or ideally 30", and 2" piping & multiport servicing 2 skimmers + 1 main drain and 2-3 returns. The MD would be off, normally, and the return eyeballs directed down but oriented to produce circular flow that would carry surface debris past the skimmers. This would be a VERY low resistance circulation system, so you'd get a lot of flow on low speed, for very low cost.
You'd operate on low speed except when cleaning or backwashing. If you want extremely clear water, you could opt for a System-3 type DE filter, preferably somewhat over-sized.
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