re: OT history and military gurus: George Washington v. Oliver Cromwell

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Who would prevail?

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Washington still prevails. As it was, the Brits' tactics and operational art were generally sound. What they didn't have (and your hypothetical time-travelling Oliver Cromwell wouldn't have solved) was priority of effort.

The English authorities did not take the American rebellion seriously at first. By the time they did, they were locked in a war (related to the U.S.-French treaty of friendship) with France (again) beginning in 1778 and with Spain in 1779. So, obviously, ragtag colonists with relatively sparse heavy guns, military training, etc., didn't concern them as much as the professional armies and navies of France and Spain.

If the colonial rebellion had been England's #1 priority during the 1770s and, particularly, the 1780s, and they hadn't been distracted by France and Spain, I have little doubt they could have prevailed.