[Al Skierkiewicz]

Well this is a tough one.
The way this competition is set up, rules are there to "level the playing field", i.e. not to allow any team an advantage. Our team sees the rules as the physical limits we must operate under, like gravity. As coaches, it is important that we teach the students that there are real world limits and constraints. There are constant meetings to discuss weight/size/function tradeoffs to stay within the rules throughout the season. There has been a real push by adult leaders to not cross the line, even if no one notices or the refs at one regional allowed it.
As to allowing teams to play with rules violations, I would have to say I'll get back to you on this one. The adults on our team spend many hours at competition helping other teams. It is our intent that if you came to play, we will help you as much as we can. I am also sure many other teams would do the same if you ask, including at Nationals. With that in mind my first response is this. With all the help and resources available, any team ought to be able to get legal by the end of the first day (practice). In rare cases there may be too much to accomplish in one day (I have seen teams go from a box of parts to a completed robot at a regional) so I would think that for those rare instances legal compliance should be completed by the end of the first day of qualifying. Under no circumstances should any safety infraction be allowed during qualifying such as the two motor to one speed controller case mentioned above. Safety First, Play Second!
I personally think it is more valuable for a student to learn how to do something within a finite universe than to learn how to bend the rules. Finally, if you think this is an impossible task, I can tell you that there is one team I have a great deal of respect for, who had a lot of work to do at a regional recently, and who with help got working and legal and won the regional.
Good Luck in Florida