I don't see why it won't work. As Perry said, it may be slow going using kettles to boil in, but I did it that way for two years and made about 2-3 gallons of syrup each year. I actually used an enameled pot designed to be used as a hot water bath for canning. I set it up on some concrete blocks, built a fire under it and boiled away. It was slow and my syrup was smokey, but it was still good in my opinion. 5 gallons of syrup may be expecting a bit much seeing as how that's over 200 gallons of sap. You'll need to have about 15 to 20 taps to get that much and if you go with the 15 gallon kettle you're going to be boiling every available moment to keep up so storage won't really be an issue. Just try to keep it in pails in the shade or bury them in snow if you've got it. Keep in mind that whatever you decide to use to boil in is going to be covered in soot so I wouldn't use good stainless stock pots from the house. Your milk jugs will fill up fast on a good day so you may need to empty them every morning and night.
As to when to tap, maybe WESTVIRGINIAMAPLE (aka. Brandon) can give some advice. He taps in WV I believe.
Homemade 2X4 w/Flat Pan
50 taps....but always looking to expand
Mostly box elders with a scattering of red, silver, & sugar maples
Allis Chalmers C & Homemade Sap Sled