TBDMS (tertbutyldimethyl silane) is your man. Its my favorite reaction, you do it in DCM or DMF (DMF supposedly gives better conversion, but I find the workup more of a pain), then just wash with water. 1.2 eq of TBDMS-Cl 2.4 eq imidazole (http://onlinelibrary.wiley.com/doi/10.1002/anie.201506253/abstract
supporting information). Literally NEVER fails and gives >80% even if you do the reaction carelessly, more if you do things carefully. If there is a lot fo "grease" from TBDMS dimer, then you can run a simple plug with hexane to elute the dimer, then push your pdt off with DCM or something polar.
TBDMS is pretty tough, it hydrolyzes VERY slowly, and can even handle weak acidic conditions sometimes. Deprotect quantitatively with a fluoride source (TBAF is popular, but aqueous KF probably does the trick too). Your hydroxylamine is a little weird to use here, but I bet it still works fine