I would think that one should upgrade weapon first, then purchase new malevolent gear. Malev gear costs less per item level than the upgrades, however, weapons directly give DPS or spell power. Also, I may be wrong, but don't weapons have more stats allocated to them than any other slot, which means more stats per point? With that, you should always upgrade the higher cost items first (2250) before lower cost items (1250) because they have a bigger stat budget. Anyone have numbers to prove or disprove this? Also assume Dreadful is already upgraded.