Microsoft Licensing

Does anyone else in a small business IT position have a hard time getting straight and complete answers from their Microsoft reseller(s) about the impending licensing change? If I choose to upgrade (WINNT-to-W2K, Exch 4-to-Exch2K, Off97-to-OffXP, etc.) when I rather than MS wishes, and one at a time rather than all at once, do I face non-compliance penalties and extra costs? How will that work?