Yes, shingles can be installed, but when a low slope, which is within the range from the manufacturers causes concern, special precautions must be taken.
If you choose to install shingles again, you should have the entire roof deck covered with Grace Ice and Water Shield.
Many inferior brands of ridge vent do leak. I use the Shingle Vent II and am out of the Carpentersville/Dundee/Elgin/Algonquin area and we have identical weather, and since I switched to this brand and properly nail it in place with 2 1/2" to 3" nails, I have not had one single complaint. The Snow Country version by GAF is very similar to the Shingle
Prior to 1991, I also used 2 other brands, Cobra Ridge Vent and Roll Vent, and each one had 2 instances of leakage.
Cosmetically, shingles will look much nicer, but when using architecturals, they vent is supposed to be caulked in place over the laminated up and down sections for a proper seal.
The ventilation is the key to preventing the impact from snow melt turning into an ice dam.
The heat tapes? Ask your local fire depertment about them. Most brands that would be supplied for a home owner are not worth it, and they will melt a pattern through the asphalt shingles.