The choice is do I go to grad school (and if so when), or do I stay where I am and keep doing this as a hobby.
The advantage to grad school is I would get to focus on the research I most enjoy instead of doing other less related things. The other core advantage of grad school is the community of like minded people who can help encourage me to perform better by sharing ideas and competition.
(What good is having a written a jukebox program that responds to the presence of my cell phone and plays different music depending on my moods, if there's no one interested to share it with)
The disadvantage to grad school is the temporary drop in income, potentially the difficulty getting in, and many of the sponsors are corporate groups who want to keep the technology under control. (Think cable companies trying to prevent the masses from posting content to the net).
The advantage of buying the condo is I get a space where I can actually install all this technology. One of the nicest things about ubicomp is that hardware keeps getting cheaper, as a result it is quite possible to personally acquire equipment comparable to what MIT media labs uses for their research. The community of like-minded people could actually be provided via the net and open source community.
Also the condo would be a far more comfortable space to live in.
I've worried a bit about whether or not to follow this ubicomp/wearable computing path. There are so many other problems that civilization needs to solve, why should I go work on this transhuman impulse?
I can come up with many justifications, but really its because that's what I do. One of the core aspects of my life is the quest for personal development--just because the world dealt you a particular hand doesn't mean you need to keep it. Since I enjoy it why not continue to push the envelope in human cognitive development.
At least I have a clearer vision of what I want to do, now the question is what path would work best for me.