I only skimmed through your post, but I'm seeing several issues. First,
voltage drop starts essentially at the main switchboard for the building. If you're taking
power at the roof
receptacle you need to take the conductors from the store's panel to the roof receptacle into account. Second, is the
transformer really 500KVA (5th from last paragraph)? Your load is 1600VA total. That's 67 amps at 24 volts. A 500KVA transformer would put out almost 21,000 amps at 24 volts. You need something more on the order of a 2KVA or 2.5KVA transformer if you use a single transformer. 500VA (not
KVA) or 750VA (not KVA) isn't enough for this load. Third, [mostly from curiosity] what type and what
gauge wire did you use for the lighting runs? Assuming an even division of 320 lamps on 5 circuits, the load per
circuit would be 13.3A.
Are you trying to start all 320 lamps at once? If so, you have a pretty hard
short circuit on the transformer secondary.
Filament resistance is extremely low until the filaments heat up. I'd suggest trying to start only one string. If that works, you might be able to start the strings sequentially. Of course, that would take time delay relays or something similar.
If I was doing this I'd be looking for a different power supply
point. 1600VA is only 13.3A at 120 volts, so just about any available receptacle in a commercial building should feed this just fine. Isn't there a landscaping receptacle closer?
Martin