... He seems to think the existing condenser is undersized. ...
That's almost never the case, especially in an older building.
First, they estimate the building's cooling load. The result of that calculation is never a nice cardinal number; it's necessary to select a condensing unit in the next standard size up. But they usually select one that's two sizes up, "just to be sure". Customers get really annoyed when an air conditioner can't cool the building on the hottest days, but not so much when the energy consumption is higher than it needs to be or the humidity control is poor.
Some years later, the original unit reaches the end of its life, they read the capacity on its nameplate and install the next size up, "just to be sure".
Some more years later, the second unit reaches the end of its life, they read the capacity on its nameplate and install the next size up, "just to be sure".
et cetera ...
(the same thing happens with heating equipment)
Twinning can provide better comfort, humidity control and energy efficiency when two different size units are installed. For example, if a 10kW and a 20kW unit is installed, you can have 10, 20 or 30 kW of cooling using only simple on-off contactors and without resorting to a VFD.