Of course it helps to also pay attention to when Phil Ligget tells you on the OLN broadcast what is coming up the next week.
Thanks for the heads-up on this -- otherwise I might have missed the coverage today.
As you discovered, trying to hand-select the episodes you want may have unintended consequences. I would suggest an auto-recording wishlist for Cycling that is set either to "First Run and Repeats" or "All (with duplicates)", and then de-selecting the episodes which you don't want. This will pick up episodes which are missed by an SP set to FRO, but allows you to leave your original SP in place.
It makes a strong visual contrast in the To Do List that way, with the episodes picked up by the SP with their double-checkmark, and the ones from the ARWL with the blue star. The blue star episodes really pop out, making them easy to find if you want to look at them.
P.S. I've seen the same guide data scenario that you described in your point #1 before -- if you have plenty of hard disk space, you can get a clean unbroken recording by just padding the initial timeslot by an hour. If you are tight on disc space, it's better to leave the two timeslots as is so you can delete the first hour after you have finished watching it.