I just want to say I admire your patience, I do know a lot of folks who would go crazy with the older games without rewind or fast forward functions.
With that said, if I were you I'd use a relatively cheap Chinese emulator that mimics as an older Nintendo handheld (check out Anbernic) and go with a DS and or a 3DS (either hacked or with a flashcart) to enjoy the two screen games properly and then just jump with the current series in the Switch.
I am actually on a similar quest right now, slowly advancing, but advancing nonetheless, this has been my journey so far:
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Beat Pokémon Yellow in a Miyoo Mini half through and finished it in my RG351V
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Pokemon Soul Silver was finished with my DS Lite, New Nintendo 3DS XL and finally my DSi XL (all progress kept with my R4 2015)
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Currently playing Pokémon Omega Ruby in a New Nintendo 3DS (the battery of the XL is kinda busted, and I wanted to give some use of my Black Friday edition for once!)
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I am gonna skip the 4th gen altogether as I "recently" finished it in my DSs.
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The fifth gen won't be skipped though, plan to use the same hardware.
You can figure out the rest, a combination of 3DS and Switch, I am honestly not excited about the Switch line though.