Multiple switching of residence status types

The situation is as follows:
Person A is currently working at an eikawa with Humanities/International Services status, but is looking at changing their job, possibly to a school/ALT type of teaching position which means switching their status to Instructor. What will happen if after some time person A wants to change jobs to an office job position or even back to eikawa? They'll obviously have to apply for Humanities status again. Theoretically, this might continue multiple times back and forth, since working with English is oddly spread over several status types.
How favourable is Immigration towards such multiple changes? Is it likely to go smoothly or they'll give the applicant some hard time after yet another change?

I'm actually surprised this situation doesn't occur more often (couldn't find many similar threads, only for one-time switch). Should person A try to keep their Humanities status (i.e. find a job within the scope) because switching back to it from Instructor one day might be harder?

As long as the jobs are legit I dont see why immigration would be difficult.

Immigration procedure would not be more difficult just because one is switching. But note that the switch can take time, and that one would not be able to start the new job until the new status is granted, whereas if one changes employers but their work stays within the same resident status category all one reports is the change in employer (then of course later to renew/extend it one needs to get the employer involved).

If you change within the permission of your current Visa you can do so.
If you change to work which is not within your current visa permission you need to apply for the correct visa. This process can take time, and you would not be applicable to work within the working field until your got your correct visa. During the change you have to wait or keep with your current job.