Hi David,
It's been done before, Cloudy Nights, the US Astro Forum has several members who have done it with reasonable success. The two main probem areas are vibration and thermal distoortion off nearby hot roof surfaces that are cooling.
Depending on circumstances piers have been built through two stories and been adequate for imaging with care. House construction is important obviously, a concrete block construction being obviously more solid that a wooden structure for example.
For visual purpose it certainly can be done, for planetary imaging using video stacking it is still workable. For DSO longer exposure imaging it would need to be pretty solid and isolated from house activities but at high ISO with a DSLR and 30 -60 second exposures, why not. Might pay to send the rest of the family to the movies maybe but it is workable. Your budget ( wish it was mine !! ) gives you some options.
I would suggest that if you cannot get a pier down through the house\garage then I would look to put very solid beams or steel across two lower floor walls that were directly above foundations. That would be the best option of isolating any floor vibrations. And image after evryone has gone to sleep.
Good luck with your idea, keep us posted if you go ahead. In these crowded living days you have to look at every option to follow your passion.
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