I used a number of figures from journal articles in my master's thesis. I cited the sources in all cases, but didn't ask permission (I didn't know at the time that I was supposed to). Many posts on this site recommend asking permission to be "better safe than sorry". In my case, the thesis is already published - should I ask for permission now, even after the thesis is published and for each of the figures?
I am not sure that one is supposed to ask permission to reproduce a picture from a book/article in their dissertation. From academic point of view, an citation is necessary and sufficient to properly acknowledge the source - otherwise it would be plagiarism.
IANAL, but I don't think there are any copyright issues here, since your thesis is a non-profit academic publication and a relatively small quote from another academic source should be normally treated as a fair use.
If it concerns a few figures only, it's not a lot of work to ask for permission post hoc. Why not? As you say, better safe than sorry. In general, when you re-print material, you always have to ask permission (if it does not pertain open access material at least).
To make it easier on yourself, I wouldn't even explain the situation to the publisher(s) you are approaching; just ask permission 'for use in a master's thesis'. Often, especially for use in undergrad theses and academic purposes in general, things are pretty lenient.
Many publishers have online resources to swiftly deal with permissions, for example through the Copyright Clearance center.
To be honest, my answer is No need, it is enough that you have specified the source.
I think some aspects of the current legal system, such as copyright, patents, etc, are inhumane and must be corrected. I think the reason you are suffering this weird issue is a reflection of the fact that the existing rules are crazy.