There's no difference as far as Windows is concerned between a USB MIDI device and a USB MIDI interface that has multiple MIDI sockets/ports. Some USB connected MIDI controllers have multiple MIDI in/out ports built in which they use for different purposes.
A dedicated MIDI interface counts towards the Wondows devices limit, but the ports it provides do not (as far as I know anyway). I've certainly had more than 10 MIDI ports active at the same time - MOTU MIDI interface with 5 ports, 2 on the UFX, 3 synths/sequencers with USB MIDI connections, internal MIDI virtual cable, control surface...
As for using multiple audio interfaces with ASIO, it's entirely dependant on whether the driver has been written to support this or not. Most drivers don't.