Many of the opinions about secondary are all-or-nothing. Some say they always transfer, others say never.
I'll transfer to secondary when
* I want to re-pitch the yeast into another batch
* I'm making additions like fruit or dry-hopping
* I just need/want to free that primary for another batch.
So good plan making room for the American ale.
Bottling day gets pretty tedious, especially alone. It's the main reason so many home brewers get kegs. Do you have an assistant? 2 batches (~100 bottles!) at once will make for a long day? Definitely doable, but maybe split them up. Timing for bottling is very flexible. When the kit says bottle in 2-weeks, it really means, "wait at least 2 weeks before bottling."
If you had another 6.5 gallon bucket, you could use it to keep the sanitizer between the two batches, and to dunk the bottles right before filling. Plus, you could use it as another primary fermenter too... More brew gear!!!