If you're right on the cusp of coverage, anything that affects signal strength becomes a lot more evident.
Multipath is really obvious in conditions like this (either picket fencing while moving or making the repeater
in one spot but not in another a few feet away.)
Also, while not huge, there are environmental effects -- I can look at the incoming power from the 300W
weather radio station 40 miles from me (line of sight, I literally can see the antenna with a telescope) and
there's a 1dB variation early morning v. late afternoon.
So those are possibilities, but given what you describe, I think it's more likely you're just not in a good location.
I'm assuming you can't actually see the repeater antenna, so you've got some ground clutter between
you and it -- that opens another can of worms. It could be as simple as someone parking a car in the
wrong spot, how wet the trees are, etc.
Both HTs and mobiles are low to the ground and the ground clutter is a serious issue. I bet on your roof,
either with a HT or with a roof mounted antenna, you would a have vastly superior signal to the repeater.