It has recently been shown that degradable linkages can be installed in the backbone of vinyl polymers via thiocarbonyl-addition ring-opening (TARO) polymerization. The objective of this thesis was to increase the scope and understanding of TARO (co)polymerization to aid in the future design of tailored TARO copolymers for specific applications. To better understand the behavior of the prototypical TARO monomer, DOT, it was copolymerized three S- and P-vinyl comonomers unlike those previously reported, yielding degradable copolymers in each case. The kinetics of the copolymerization were studied for two of the monomers, and post-polymerization oxidation of one copolymer was used to convert it to one of the other copolymer-types being simultaneously studied. Vinyl ketone monomers are known to yield photodegradable polymers, motivating the investigation of a copolymer between DOT and MVK. These copolymers were successfully synthesized using both RAFT and free-radical methods. Kinetics data showed the copolymerization was ideal at a 90:10 feed ratio, and this was supported by a series of differing length copolymer with equal feed ratios degrading to (near) identical distributions. The copolymers were orthogonally degradable by aminolysis and photolysis, with the smallest degradation fragments produced by aminolysis followed by photolysis. Finally, a novel cyclic xanthate monomer (BOT) was synthesized using thiophosgene, avoiding the common but troublesome thionation step used to synthesize TARO monomers. BOT was found to homopolymerize (with a 37% conversion), as well as copolymerize with DMA and styrene (albeit inefficiently in the latter case). All (co)polymers were degradable by aminolysis, and DMA copolymers were degraded with aqueous NaOH. The dithiocarbonate linkages installed in the backbone mean the degradant is not retained as the fragment’s end group, which is the default case for other TARO (co)polymers.