FWIW, there is a significant difference between Feather and ItsyBitsy boards distinct from size and number of pins: how the board is powered.
By design, Feather boards can only by powered by an on-board LiPo (the VBAT pin can't be used for 3V3 input) or via USB 5V (the docs explicitly warn against using the 5V VUSB pin for input power from a non-USB source).
The ItsyBitsy, on the other hand, has a VBAT input pin that can accept anything from 3V5 to 6V, as well as a 3V regulated output.
So, if you have a design with one MCU and a few peripherals that don't exceed the current that the LiPo from the Feather can provide (or you're tethered to USB power) then Feather is great.
But if your power source is, say, a 12V battery that you need elsewhere for a high current load, you may want to supply your MCU(s) with 5V from that battery. In this case, you'll have to use the ItsyBitsy form factor instead.