It does sound like he has 2 parallel service disconnects grouped on that maypole. That would allow 400a. On the line side of the service disconnect, it is all up to the power company what they want to run. I have seen the PoCo bring the same triplex they use for a 200, to a
320 or 400 service. It is up to the customer to complain that they have low voltage before the PoCo will act. They are eating the I2R losses for that smoking power drop. They usually do size an underground lateral using 310.15(B)(6) but that is still smaller than you get with the regular 310.16 ampacity table.They are not really serious about wire size until you get to commercial because most homeowners greatly overestimate their power usage ... unless it is Al Gore. ;-)
If you averaged 100a your bill would be almost $2600 a month at .15 a KWH. The PoCo engineering department can see your bill. If it got that big, the DEA would be breaking down your door looking for a grow operation.