Your configuration makes my brain hurt, but try this:
...when in the field and doing a setup...
148) connect the single LNB from the Dish 500 through your meter directly to your 301.
Use the meter to align to the satellite.
You may need to run a switch check with no LNBs connected, then connect the above and run the check again, but that's just if you have trouble identifying your bird.
To make aligning the dish 500 easier, consider replacing the Y adapter holding your LNB with an
I adapter.
If you insist on using the existing Y adapter, just set the skew to 0, 90, or whatever
straight up is (no skew).

Aim the LNB arm to the 148 bird (taking into account the local magnetic variation), and then move it 4.5 degrees more east.
(move LNB eastward a bit, or rotate the dish on the mast a bit counterclockwise, looking down on it from above).
You should find your 148 bird easily with that meter, if your elevation is correct.
110/119) you seem to be able to dial in your dish 1000 pretty well.
If that's so, do it, then connect the 148 LNB to it, and run your switch test again.
I could have been more detailed, but you seem to have a pretty good handle on things, and I hope the above tips will be sufficient.
Let us know.
