Recent advancements in music source separation (MSS) have focused in the multi-timbral case, with existing architectures tailored for the separation of distinct instruments, overlooking thus the challenge of separating instruments with similar timbral characteristics. Addressing this gap, our work focuses on monotimbral MSS, specifically within the context of classical guitar duets. To this end, we introduce the GuitarDuets dataset, featuring a combined total of approximately 3 hours of real and synthesized classical guitar duet recordings, as well as note-level annotations of the synthesized duets. We perform an extensive cross-dataset evaluation by adapting Demucs, a state-of-the-art MSS architecture, to monotimbral source separation. Furthermore, we develop a joint permutation-invariant transcription and separation framework, to exploit note event predictions as auxiliary information. Our results indicate that utilizing both the real and synthesized subsets of GuitarDuets leads to improved separation performance in an independently recorded test set compared to existing multi-track guitar datasets. We also find that while the availability of ground-truth note labels greatly helps the performance of the separation network, the predicted note estimates result only in marginal improvement. Finally, we discuss the suitability of commonly utilized metrics, such as SDR and SI-SDR, in the context of monotimbral MSS.