Thanks y'all! @Leon L., all that info is especially helpful. Your FAR max is the same one I got, though I've also seen variances awarded for FAR and setbacks - though in those case it was mostly to appease neighbors opposing the construction.
So familiar with MX3 and seen what they've sold for. They're often atrociously ugly, too! We'll be getting some cost estimates from the architect, so I'll be able to update the construction cost, but yes - that would still be a good return — at least covering the cost of the addition on the main house and giving us a nice lump of profit.
Leasing would definitely be a pain. I think of the advantage there being that if we held it for a while (15 years?) the value would increase enough to make it worth our while, especially since the rental #s look like they'd cover the mortgage in the meantime. That said, leaning towards condo regime and selling, so it's good to hear you think that makes sense.
Historic preservation completely limits demolition. We've already done major renovations - new foundation, geothermal HVAC, completely new kitchen & interior, etc. etc. so I think our buyer pool would just shift towards people looking for the ever-rarer historic house that isn't a tear-down in our neighborhood. Our work, 10+ years of sweat equity, is very high quality, so it really wouldn't make sense to tear down unless zoning completely changed and the lot could have an apartment building on it. :) Also, we are surrounded by 5 historic, well-preserved houses, so it's really the only "cluster" left in our hood. It seems like there is a market for that, don't you think?