Preferably only spending once.There are very few professionals that will get past 295 on factory heads and those that can flow that well usually crack fairly quickly. So I think the 285 is realistic at least.
Been there, done that. After investing more than the cost of a set of aluminum heads and filling 5 out of 8 cylinders with Dextron. I was fortunate enough to be able to donate the cracked heads to a DARE program and write them off on my taxes as well as my things I learned the hard way list.