Hi Nawazish,
https://wiki.xnat.org/xnat-tools/subject-and-session-labeling-schemes-for-uploads - The XNAT Desktop Client has several ways you can assign a subject label. If you consistently use the same mechanism, and the value remains consistent over time (for example, using Patient ID, and the Patient ID remaining consist over time), the additional studies should get associated to the same subject in XNAT. Note that the "Auto-Generate Labels" option for subject labels has exactly this scenario as for why that option will not be a good choice for your scenario: when you come back in a month and upload new longitudinal data, it's going to autogenerate a new random ID.
On number 2, the desktop client is not equipped to act as a way to package and upload arbitrary data. That sounds like a very difficult task to solve. XNAT does have APIs for uploading arbitrary resource files where you could store these, or you could create new data types to model the data if you'd like it to be searchable.
Thanks,
Charlie Moore