In this paper, the performance boundaries and corresponding tradeoffs of a complex dual-mode class-C/D voltage-controlled oscillator (VCO) are extended using a framework for the automatic sizing of radio frequency integrated circuit blocks, where an all-inclusive test bench formulation enhanced with an additional measurement processing system enables the optimization of 'everything at once' toward its true optimal tradeoffs. VCOs embedded in the state-of-the-art multistandard transceivers must comply with extremely high performance and ultralow power requirements for modern cellular and Internet of Things applications. However, the proper analysis of the design tradeoffs is tedious and impractical, as a large amount of conflicting performance figures obtained from multiple modes, test benches, and/or analysis must be considered simultaneously. Here, the dual-mode design and optimization conducted provided 287 design solutions with figures of merit above 192 dBc/Hz, where the power consumption varies from 0.134 to 1.333 mW, the phase noise at 10 MHz from -133.89 to -142.51 dBc/Hz, and the frequency pushing from 2 to 500 MHz/V, on the worst case of the tuning range. These results pushed this circuit design to its performance limits on a 65-nm CMOS technology, reducing 49% of the power consumption of the original design while also showing its potential for ultralow power with more than 93% reduction. In addition, worst case corner criteria were also performed on the top of the worst case tuning range optimization, taking the problem to a human-untrea table LXVI-D performance space.