Legal to start, legal to finish. The key phrase in this reg is "may not accept an assignment yadda yadda yadda". You can't accept an assignment that violates the 10 hours of rest in 24 rule. Then it depends how your company does your assignment. Flight Express does my entire night at once. Some may do it leg by leg I guess.
I accept an assignment on Monday with a duty on time at 2030, flight is proposed to leave at and arrive at 2345. Leave again at 0640 and arrive back to base at 0855, duty off at 0910. 12.7 hours duty time.
This is my proposal every night, unless there was an issue with the previous night.(long duty periods like this can have 8 in 24 issues for flight time).
Using an extreme example, on this particular night, I arrive at my destination on-time, but the guy that takes my stuff out and back runs really late. I don't get re-proposed because the other guy is late. We go off the original proposal(assignment). Anyways, I don't leave until 0900 and arrive back to base at 1100, duty off at 1115. I've gone over 14 hours by 45 minutes. The legal issue isn't that I've gone over, it's when I can accept the next assignment. On Tuesday night, It would be illegal for Flight express to assign my line with the normal 2030 duty on time. I would have only received 9 hours and 15 minutes of rest. It would be illegal for me to accept this assignment as well. So the earliest duty on proposal I could accept would be 2115. This would cause an absolute mess and by the end of the week, I'd be doing day runs! haha So dutying off after 1030 is avoided at all costs if possible.
This applies to the flight time rule as well. Again, the key phrase is "the assignment can't exceed blah blah blah". When I do my Wichita runs in addition to my normal run, my proposals are always 7 hours and 58 minutes. Usually the actual flight time is around 7 hours and 30 minutes, but has gone over 8 a couple times, which just requires additional rest depending on how much over it goes.