Pearl Izumi (PI) skull cap.
Long sleeve and maybe short sleeve Craft undershirt
PI Elite Softshell HiViz jacket
Voler Jet HiViz jacket
PI Thermal Barrier tight (no pad) or Performance Triflex tight (no pad, heavier but cheaper)
Sugoi Resistor booties
Performance Zonda gloves
Add Performance leg and arm warmers for spring and fall.
That should get close to your budget - you might have to forgo the PI Softshell and just wear two SS jerseys with arm warmers. That'll mostly work.
The Zonda gloves are good down to ~40° and raining. Colder than that you have to spend real money. GoreTex or Giro waterproof.
Use toe warmers to make up for not wearing $300 MTB boots.
Put plastic produce bags with the bottoms cut out under your booties and wrapped tight around your bare leg to keep water out of your shoes. Or better, go to a dive shop and buy a pair of dry suit leg seals. Put them on your bare legs, over your bootie tops. They're not expensive.