Or search: gauge, guess, assess, cipher, cypher, esteem, reckon, compute, lowball, scalage, figuring, forecast, guessing, truncate, misgauge
2 Syllables: SU
Everett, separate
3 Syllables: SUU
baronet, celebrate, decorate, dedicate, deficit, definite, delegate, delicate, deprecate, desolate, educate, elevate, emanate, emigrate, estimates, etiquette, Federalist, generate, hesitate, meditate, Methodist, penetrate, predicate, prejudiced, requisite, resume, segregate, separates, venerate
4 Syllables: USUU
accelerate, commemorate, confederate, Connecticut, degenerate, disseminate, indefinite, interrogate, investigate, inveterate, necessitate, perpetuate, prerequisite, regenerate
5 Syllables: UUSUU
overestimate, underestimate

Found 47 words across 4 groupings. Skipped 18 excess words of a similar stem.