Your questions are a bit generic...but there is a ton of info here...just search under the topic you choose....as to your questions
1-you do not need a cutter to design your shirts
2-cutter you will use to cut heat press vinyl....only vectors can be cut or contour cut with optic eye
3-if using Corel there are very few places with classes..it comes with tutorials and lots on YouTube
4-to do rhinestones..you need a program or plug for Corel...which I don't like
5-to make the templates you need either a cutter or dedicated cam machine
6-you can always outsource
7-to do logos you gave to have vector image..or vectorize the bitmap
1-you do not need a cutter to design your shirts
2-cutter you will use to cut heat press vinyl....only vectors can be cut or contour cut with optic eye
3-if using Corel there are very few places with classes..it comes with tutorials and lots on YouTube
4-to do rhinestones..you need a program or plug for Corel...which I don't like
5-to make the templates you need either a cutter or dedicated cam machine
6-you can always outsource
7-to do logos you gave to have vector image..or vectorize the bitmap