The weather is included automatically with every down loaded position report when using data link which almost everyone has these days.
Nope. Not all position reports are automated, and "almost everyone" doesn't use them.
If a flight is using CPDLC, then you wouldn't hear his HF position reports in any case. If you do hear the position reports, you should hear the Met (SAT/wind) portion on random-track reports and at designated points (NOPAC tracks) and/or "as requested" (Atlantic). If you don't, the pilots are either ignorant or unprofessional when they omit them.
Also, in partial answer to the OP's question, airline dispatchers and flight planning systems account for wind forecasts. IIRC, full forecast headwind components must be considered for fuel burn, but only 50% of tailwind is allowed for "credit."