AQ: Transformer uprating
I once uprated a set of 3x 500KVA 11/.433kv ONAN transformers to 800KVA simply by fitting bigger radiators. This was with the manufacturers blessing. (not hermetically sealed – there were significant logistical difficulties in changing the transformers, so this was an easy option). Limiting factor was not the cooling but the magnetic saturation of the core at the higher rating. All the comments about uprating the associated equipment are relevant, particularly on the LV side. Increase in HV amps is minimal. Pragmatically, if you can keep the top oil temperature down you will survive for at least a few years. Best practice of course is to change the transformer!
It is true that you can overload your transformer say 125 %, 150 % or even greater on a certain length of time but every instance of that overloading condition reflects a degradation on the life of your transformer winding insulation. Overload your transformer and you also shorten the life of your winding insulation. The oil temperature indicated on the temperature gauge of the transformer is much lower than the hotspot temperature of the transformer winding which is a critical issue when considering the life of the winding insulation. Transformers having rating of 300 KVA most probably do not even have temperature indicating gauge. The main concern is how effectively can you lower the hotspot temperature in order that it does not significantly take away some of the useful life of your transformer winding insulation.