In answer to your question: Maybe?
There are a number of RS232-to-"wireless" technologies whereby you could likely use DEBUG and the programming port to "send signals to [your] computer." Getting it to the computer, regardless of where they are in the house, may prove a challenge.
The other thing that will be hard is for your BoeBot to figure out where it is. There are all sorts of sensors that you can add that will help like wheel encoders, maybe a compass, maybe a PING distance sensor. You can also add an accelerometer and a gyroscope. Every bit of position information helps. None of this works with the existing BoeBot software. All of these sensors do come with examples that you can use to write your own BoeBot software or modify existing programs. "Roaming with the BoeBot Robot" is one program that uses a PING to detect obstacles so the BoeBot can wander around a room or rooms in a house.
The FlashFly / Blue Wolf combination would certainly provide a wireless link. Danow would still have to write / modify programs to figure out (approximately) where they're at and communicate that to a base station (PC).
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In answer to your question: Maybe?
There are a number of RS232-to-"wireless" technologies whereby you could likely use DEBUG and the programming port to "send signals to [your] computer." Getting it to the computer, regardless of where they are in the house, may prove a challenge.
Would the new FlashFly cum Blue Wolf combination meet the bill?
I know it's difficult to say absolutely, but does the FlashFly combo have sufficient power?