The use of single sideband (SSB) signals and envelope detection is a promising approach to enable the use of economic free-running lasers in photonic THz communications. To combat the signal-signal beat interference (SSBI) associated with envelope detection, broad guard bands (GBs) may be used given the large unregulated spectrum available at THz frequencies (100 GHz-10 THz). In this scenario, the conventional way of generating SSB signals through a digital SSB filter (here referred to as the CSSB scheme) would require quite high analog digital-to-analog converter (DAC) bandwidths. Digital virtual SSB (DVSSB) and analog virtual SSB (AVSSB) have been proposed in directdetection optical systems for relaxing the DAC bandwidth requirements. In this paper, we compare the three techniques through simulations and implement them, for the first time, in a THz-over-fiber (ToF) system operating at 250 GHz. For the transmission experiments we employ 5 GBd 16-QAM signals with three different GBs (5.5 GHz, 4.75 GHz and 3.5 GHz). The simulations show that the best performance is obtained with the AVSSB technique, while the worst is obtained with the DVSSB scheme, where the quality of the generated sideband degrades with carrier-to-sideband power ratio. In the experimental transmissions, where receiver noise was the main source of noise, similar behavior was found between the three techniques. At the 3.5 GHz GB, however, the DVSSB exhibited a penalty of 1 dB with respect to the other two. This is likely to be due to nonlinear distortions caused by the increase in the virtual tone power.