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3-piece wheels have the tendency to leak. They can develop leaks over time through the split ring seam or through the valve stem if it's a multi-piece stem vs a rubber grommet type. Your old tires may have been leaking through one of these paths. It would be odd for all 4 to leak flat at such low mileage without another flaw present. My guess is the tech who put 4 new tires on has solved this leak issue.
Insulated from the concrete? Like the tires do? How cold of a storage area are you talking? Cars are designed to handle pretty large temperature swings. Think -40F to +120F. I would assume the car will be stored at somewhere between +50 to +70F, in which case I think you may be over thinking this. The guy letting his car's ankle show likely has a lift in there to get up and over with the wood blocks.
The tender can go anywhere it fits and won't fall or rub. I go back and forth between my charger being on the floor or in the frunk depending on what's going on around the car.
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