Different materials have different reflection and attenuation effects on radio waves. If you have a wall between you and the access point, the received signal will be different depending on whether it is a concrete or wooden wall. Similarly, if a house off to the side has nice aluminum siding, it could act as a reflector and bounce a signal around an obstruction. The effect of all of this depends on the geometry of your layout. Now the accuracies you are after appear more like determining which house something is in instead of which room, so these effects might not matter all that much. If nothing else, it sounds like it would be fun to try it out.
I did stumble upon this paper that spells out the problem pretty nicely, though it is a bit different than your situation. That paper starts with known access point locations and is trying to find the mobile user. In what you propose, you become the access points by moving to known locations, such as the corners of your neighborhood.
A more pessimistic evaluation of wifi triangulation is found in this thread, which not only mentions the problems associated with having a variety of "stuff" around that can confuse your signal, but it also takes into consideration more as to how these wireless access cards work (i.e., the signal you see reported on your laptop might not be indicative of the true signal because it might be considering only the valid data it receives).
In any event, what you are proposing and what you are expecting all sound reasonable. Certainly it is easy enough to try. I would start just by considering a known access point, such as one in your house, to see if it would work. A rough start would be to consider that pdf I linked above and set n=1, S=0, and Lw=0 in their Equation 3. Calculate a d (distance) for each corner of your block, draw circles around each location with radii equal to d, and see where they all intersect (you could also figure it out analytically by finding where the circles intersect by coming up with the equation of each circle (make one of them at the origin to simplify it a bit) and finding their intersections).
If you were going to try it out, I would do as you suggest by taking a number of values at each point and averaging them to knock down the variability in the received signal. I would also move the laptop around withing a couple meter box as the data were being taken to help and try to smooth out subtle multipath issues you might get. If you take some data, post it; it would be fun to play with the data.