Diploma

You can either go for job or take lateral admission in 2 year of BTech offered by few Engineering Institutes.

Yes, but you will have to go through the same standard route again ie by appearing the requisite exams nad exceling in the result. Alternatively I would suggest to you that you do a degree course from some other state college which takes diploma holders, then try to do M.Tech from an IIT.

Yes, You Can Go with this Two Certifiacte courses at same time. Now UGC has Allowed Students to Go with Two Degrees Couses for the Better employability and For enchancement of Skills and knowledge

Hello,
I will advice you to continue to a master degree after your PG Diploma. A number of universities and colleges offer what is known as lateral entry programs. You can gain entry into a master degree program after completing your PG Diploma. You can contact the concerned university to know more a

You need to select core technical subjects like mechanics to go into supply chain. After 10th you dont have such specialist options.Core branches like Civil, electronics, IT, Comp Science are available. You can do MbA in logistics after your graduation, only that will make sense and addvalue.