Ross,
I make no pretenses about being anywhere close to a horticulturalist... plus, except for two years working narcotics in Alaska, I have been blessed to enjoy my 45 working years in terribly temperate climates; so I am certainly no judge of overwintering techniques. But this guy sure seems to talk a good game, as if he maybe knew a thing or two about this topic; and he is in Ohio... does Philly get that much colder?
To make a shot in the dark towards solving your temperature dilemma, my first thought went to using a timer to activate the type of battery blankets that we used in North Pole, AK for say, 20 minutes each hour.
http://www.amazon.com/10952544-Battery-Heater-Blanket-Watt/dp/B000FE7IIS/ref=pd_sim_263_7?ie=UTF8&dpID=51a%2BFjToKML&dpSrc=sims&preST=_AC_UL160_SR160%2C160_&refRID=01CDCWR3A7MRN50QH7QS
To gain the insulation needed to keep this working, I thought of maybe using a slightly smaller bucket inside the 5 gal bucket and wrapping the battery blanket around this smaller one.
Another idea might be to not use the bucket at all, but instead use a thrift-store purchased ice-chest to hold the cuttings and planting soil. This could be stored in the garage, mud room, etc. and an auto heating pad
http://www.amazon.com/Kats-22400-Watt-Battery-Heater/dp/B000I8XDAS/ref=pd_sim_263_6?ie=UTF8&dpID=41RYj8NSKDL&dpSrc=sims&preST=_AC_UL160_SR160%2C160_&refRID=1W5WNRRK8V71YPTATQ0R
used with a timer for a few minutes every couple of hours, to maintain 40* or so. About April, pull the ice-chest out into the sun and open it up on nice days to warm the soil inside even more. By May... you have the rooted cuttings that your seeking.
Again, Just a WAG... good luck,
Blue