Tails is the term to describe the conductors connecting the secondary windings to the LV TX CB. By using the term tails, you have less confusion. Tails, feeders, pilots etc...they are all conductors, but you use different words so you are clear what you mean, because they are for different things.
When you look at the cost, have you considered everything? Digging up land, installing, jointing, testing, comissioning, reinstating land.
Running another parallel set of cables just seems like a bodge to me. You are better putting in the right cable for the job.
The person that installed this needs shot. You have a 250A load. If this is total, split across three phases, then what size is the cable, 35mm? (more to the point, what size is the TX? Is it just a tiny 100KVA sat up on a pole or in a little cabinet?Bodging the job again will only give you grief in the future.
you say if the cable (c) is damaged, it shuts down the show - what happens if you lose one of the cables if you have two sets? Same problem (well you would lose some load). I assume they will be in the same trench, so if one gets damaged, its possible they both will be. And what is going to damage them? What sort of land is the cable crossing? Are people likely to be digging around the place? Put the cable in some rigi-duct for some protection, with plenty of yellow tape six inches above that.
Your last question. If the load was 1MW and this was via the 11kV network, you would either have two 750KVA transformers or a large 2 MVA transformer. Previous option is best, because during maintenance, you can take one side out (reducing the load to essentials only so the TX can take it). Larger TXs (above 750KVA) give you larger short circuit currents, and you need better, more robust protection. All adds to the cost.
But in general, if the load increases, and the original supply is not up to the job you get a new supply and pay for it. Simple as that. Its why you need to think about the future when installing your network, and ensure you have a few spare ways on your LV board and a TX with plenty of spare capacity. The different price of the hardware is not the real cost. The cost is the man hours and time installing it.
I had a job a few years ago where a land owner is Sussex wanted a water pump for his polo fields. The nearest available line was a 33kV line a mile away across the downs and through a forest. It cost him hundreds of thousands of pounds and took over a year to get through wayleaves.