Without seeing exactly what you are doing, it's hard to say. Wood can be tricky. Sometimes it requires cutting in the opposite direction. In some cases, I've use Left handed tools to be able to do a production job at higher speeds without getting tearout.
One option may be able to make multiple, shallower passes. Oak is probably not your best choice.
Maybe a little, but probably not much.- Will a multi-flute but help in preventing chip out, up/down cut?
As fast as possible, to maximize tool life. And as slow as you need, to get the finish quality that you are looking for.- Does anyone have recommendations on feeds and speeds?
Generally, the harder the wood, the cleaner the cuts. Closed poor woods like maple will "splinter" much less than woods like oak, but maple can tear out badly in other situations.- What's your opinion on the best wood when requiring engraving detail?