Drove 40 miles to scrounge.

I would not rent a trailer. Unless this is you last winter burning wood. You need to buy a bigger trailer. Not a lot bigger ... I understand you are pulling it with a jeep. Just a little bit bigger maybe a 5X8 It will double your haul and save you trips.
On the other hand you said your wood guy costs $45 truckload? If I could get wood that cheap (Assuming your talking about a full size pickup truck) I might buy instead of cutting for myself. That's about half of the going rate around here. That's why I haven't bought wood in at least the last 10 years.