Do you think there will ever be a time when we can power down the switch, then power it up and still be in CFW, without having to send the payload again with the jig/USB PC thing?
Unfortunately as is the current affairs and state of the switch hacking scene no, we can't have the convenience of coldboot CFW (like with the 3DS or PSP). something as such just doesn't seem feasible as of yet. We never know when or if it'll become a possibility in the near future though. That's up to the developers hard work and effort put into achieving such glorious feat. Again, keep in mind that the Dev guys do all of the great hackery work/service for free to deliver greatness to us, so we shouldn't pressure them but rather be grateful for what we've currently got.
With all that said though, there's this "modchip" way of hacking things(though it's not a real modchips, hence the quotation implies)
By attaching something to the switches motherboard you can launch payloads directly, hereby allowing you to have a "coldboot" (kinda)
See here and check this out this guide for more insight regarding your inquiry.
Do you think there will ever be a time when we can power down the switch, then power it up and still be in CFW, without having to send the payload again with the jig/USB PC thing?
As stated above, AutoRCM plus a modchip will accomplish what you want.
There are convenient ways to push fusee-gelee payloads, such as using an Android phone, USB dongle, etc.
The Switch should rarely be powered off. If you keep it in sleep mode when you're not using it, this isn't much of an issue.
That all being said, Switch systems on 3.x and lower might be able to get an untethered coldboot exploit someday in the very distant future. Other than that, the above is probably all you have.