I don't doubt your mechanical skills and I also don't think that the filter is a problem. When tightening the filter, I always turn it until there is tension and then turn the filter another 1/2 turn. Some would say that a full turn is needed, but then trying to get it off becomes much to hard.
Be careful with a filter wrench. First, it is difficult to get a wrench on it because of the limited space. Second, if it is too tight, you will never get it off.
The amount of oil on the new seal should be just a coating. Wet your gloved finger and rub the oil onto the seal. It should appear damp without any oil dripping into the groove.
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Keeping it running is better than buying new
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