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30 day trip central Europe advice needed

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Hello! I am brand new to Fodors and new to planning a trip like this. I have been wanting to backpack Europe for ages and and finally going to do it. I have several questions and would appreciate any advice or pro tips anyone can offer! Thanks in advance!
I am aiming for 30(ish) days total including flights from Boston, MA.

Destinations: Prague, Austria (*Vienna), Switzerland (*Geneva, Interlaken area, Bern), Germany (Bavaria and Black Forrest to visit my ancestry roots, and Munich are priorities), Belgium ( Bruges or Brussels?) then to Amsterdam for a week to meet my family and Scotland via plane for a few more days. I think I have The Netherlands and Scotland legs sorted out.

At this point I am getting bogged down by the easiest path to these locations. I plan to go in the Spring (April or May) so I was thinking either start south (Switzerland) and move north, or possibly start East and move West ie: Prague, Austria, Germany, Switzerland, Germany again, Belgium and finally Netherlands etc.
Deciding the path is obviously huge, any advice would be great!

Secondly what makes the most sense in terms of budget and ease for transportation? I am very confused by the train system- I think I am overloaded on info and it's probably very simple. It seems there are government run trains and then local systems- seemingly the same routes but a vast difference in $$? Does a *Swiss Pass make sense? I am open to short plane trips as well if it makes the most sense.

I am planning on staying in Hostels so any suggestions there which align with possible destinations would be great!

Lastly- I am only bringing a backpack and would like to hike in the aAlps- possibly Gimmelwald area (there is a recommended hostel there) do I actually need hiking shoes specifically? That may be a bit of an odd question- I just want to be properly prepared since I'll have so little room to pack.

Anything I need to omit from the itinerary or anything I must not miss- please advise.
thank you!!

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