I've done both, and in my opinion, accumulating enough money to buy a rare is harder than getting 99 in certain skills. I would buy a rare, in the long-term it will be a good investment. If you really want a 99 skill though you could do one like fletching and have more money than you started with and then buy a rare. But there's no reason to buy all of your skill items at once. You could buy a rare then buy logs, etc in installments. Process, sell, buy, continue.