My question, do you think running the generator for a 2-3 hours a day will be enough? or am i going to kill my group 31?
It won't be 100% full after 3 hours but you won't kill it, either. It wouldn't hurt bringing it to 14.6V and/or equalize at home after that week. It will last longer then.
I've been thinking of getting a 2nd grp 31, or just take along my 10 year old grp 27.
Get the 2nd Gr31 if the 1st one is not too old yet. Two 31 will discharge shallow-er than a single 31, they will last more years. Otherwise, run the existing gr31 to death and then buy two 31. Leave old Gr 27 home.
If i upgrade charging, should i just get the progressive dynamics?
Good idea. It will preserve batteries better than WFCO on shore power as well.
As noted, another alternative is to do nothing. Your loads are low, the battery(s) will likely die of old age before you notice the diminished capacity after years of mishandling.
I hear your pain of Canadian shopping. If you are close to the border, consider opening an account in private shipping/receiving outlet on the US side of the border. Can be done online, you'll get a US street address, and pay a few bucks when parcel arrives. Many people in Vancouver are doing this. Better prices and lower shipping cost then directly to Canada. They keep it for you for 2-4 weeks (depends on the outlet), then start charging storage fee. Sometimes there is an annual fee, but here in coastal WA it's usually zero, too much competition :)