Bacffin, you have a pretty favorable TVFool plot. I live in southern New Hampshire on a hill surrounded by red pines, oaks, and maples. I can affirm your suspicion that wind and rain can impact reception.
Looking at the green band of stations from your report and ignoring nonchannels and spanish language channels, you should be able to get good reception with an indoor antenna pointed to 145 degrees. I think you should be able to pull in WENH and WMUR with a vhf antenna pointed to 5 degrees as well. I'd probably look at joining a y10-7-13 to a 91xg. Since you already own the HD9095P, I would consider testing/coupling this with a y10-7-13.
For test and pointing purposes, I like to use a HD Homerun HDHR3-US because it reports signal strength, signal quality, and symbol quality on two channels concurrently. These cost $50-$60 and have other uses...
If you want to take the black box approach, you can point the antenna with a compass and move it around until things look good.
Get two long pieces of factory terminated RG6 coax and run it directly from the antenna to a television. If that works, you do not need amplifiers except to account for distribution losses and your antenna is good. Move the coax from the input of your TV to the input of your splitter. Terminate all outputs except for one and use the second coax to connect directly from the splitter to a tv. If this is fine, replace your factory coax with the premise coax. If the signal is worse, replace the premise coax. Use this iterative approach to test each leg of your infrastructure repairing any deficiencies.