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Looking at google street view, it looks like you'll be encountering some long climbs up to 5% grade, with most of the hills being in the 3% range. Considering your weight, that eliminates 250w motors totally. 350w motors would climb up the 5% with your weight, but might melt from the effort. Overheating is the real problem.
Really you need a minimum of a 500w motor. In this case, it's not for the added power, but for the added ability to handle heat and strain. Bigger is tougher. Tougher lasts longer.
You want "Rock solid dependability", that eliminates the gear drive motors, though you might want to reconsider a bit.
Gear drives from the vendors I listed will in the "Very dependable" category. Less dependable than a "Rock solid dependabile" direct drive with only 1 moving part, but still very dependable. The advantages of the gear drives are lower weight, freewheel action when you don't want to use them, and more starting torque.
The direct drives advantages are near silent operation, higher cruising efficiency, and near total reliability. They also have some advantages that you personally don't seem to need, like being capable of going much faster, being more powerful, and taking huge heat loads from climbing or hauling or general hooligan abuse.