We and another neighbour did object to a third neighbour's submitted PP application and in the end we won and the proposed development did not go ahead. We had the advantage of the planners being on our side, and having another very vocal neighbour also objecting. In our case the grounds for opposition were clear cut. We had to submit a very detailed and well worded objection, which mentioned many points. The refusal was based on what we had thought of as the least of those points. There was an official hearing, all very formal, and now our neighbour no longer speaks to us, which is something else to consider. For a previous application for another development, we had told our neighbour that we would not object, but for this second plan we told him we would, which seems fair.
Have you discussed the details of your rich neighbour's proposal with him? It could be that if he knows you will object, that he will consider renovating rather than rebuilding in his initial application.
However, don't assume that because your developer has done this before, that he has the planners on his side. Of course it depends on your local council, but planners can take great offence when they feel they are being taken for granted by developers.
So my first advice would be to research the local planning laws and see where you might have a fair and legal objection. It could be that your success might only be that he has to renovate and convert the original steading buildings rather than demolish and put up new houses, but for the character of the houses that would be worthwhile, even if you can't prevent some work being done.
A great word to use in discussions is "vernacular" ie the local style. So you might say that the proposed architectural drawings are not in the local vernacular, for example they are two storey ranch-style houses, when the local style is single storey cottages.