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I just got a few things sorted out within my mind space.
The onus is always on the particular hardware one has in hand. In the end, software is just a way to direct the hardware.
Even if using emulation. This can only be a temporary thing, for the REAL lover. Or a way to practice skills while being away or barred from using the hardware in question. 
If one is serious about it, emulation is not a permanent or isolated activity
Rationally spoken there are two reasons for retro computing: conserving hardware and / or conserving software
And conserving the usage of both

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I think using the classic hardware with the classic software is the best thing to do, second is truthful emulation of older software and hardware (temporarily), third is using newer software on fitting hardware, that enables the older software to run. 
The first option requires you to have at least one other device that is running contemporary software, so that you can take the unavoidable frustration that comes with trying to do vintage computing gradually, when one has the time / energy.  I do not have old hardware here,  at the moment, where I am, so the first and best option is  already out of the window.  The second option is emulation until I can get the real deal.
The third and last option is about using OSes like Pimiga, Aros and the AmigaBSD thing, or FreeDOS, for DOS, on a modern computer. 
With the third option, is still necessary to have one other device running a reliable OS, because even though these options sound like good news, they also always have their own specific problems. 
Emulation is the most convenient and safe solution, but one risks to not take it seriously enough and rely too much on the host system.

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In any case, if one is to do retro, one has to suffer. I do not think there is a way around this. But gradually one can overcome much of the pain and inconvenience by stacking up solutions. But for this one has to be steadfast and stick with one system, no matter the issues and frustration. 
In fact, I have just switched emulation to second position, as a temporary preparation to using accurate hardware
Personally I think the third option is not a true option. It keeps one from actually using the classic hardware and software as it was meant to be and one ends up with a mixed bag, a semi modern system that can run some older software.  This option is mediocre for modern use as well as for classic use. It is a false solution. To me this is the least attractive.

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