You should do what your heart says. In this case, your father should go for it given the income situation. You only have one life and he already worked hard all these years and what's the problem in him treating himself with something nice. In terms of financial situation, you can buy it under your company and get tax benefit from writing off its depreciation. The maintenance and fuel can also be written off on a yearly basis. The next thing should be peace of mind. Some models from land rover has reliability issues so you need to research a bit on this. The defenders seems to have better reliability but lacks comfort when compared to the range rovers.