Why not start with your favorites. Perhaps commence with photos taken in 2017 and then 2016 etc.
If you organize images in folders you can import each one separately and that will enable you to create a named album for each import batch.
The link below with video tutorials, has a good overview.
That could be a starting point, to either work backwards or start with the earliest and work to the present. separating them before working on them with LR?
It would seem that the mess is mine to fix as I have a few years of pictures that some where just dropped in folders that I named with a date. Earlier pictures have folders that I did with subjects, like son, grandchildren, friends, background ect... that have been taken over time but has a lot of different dates that span years. Until lately my organization skills where done on the fly and I am going to pay for it now
I guess I need to try and do some more research to answer more questions like "do all photos imported into LR upload to the cloud?" if I try to work on these in segments "can I choose what goes to the cloud?" "or any photo I edit go into cloud as there is no other choice?" "what if the folder I work on has total space greater then I have on the cloud"
I am seeing that the poor skills are going to haunt me for awhile until I get things organized and have some since of order.
All photos imported into LRCC will go to the cloud. But it is possible to permanently delete photos from the cloud if they are unwanted, in order to free up more space for others.
if I delete any from the cloud will it effect what is on my drive? example: I import a folder that has less then 20g and do what edits I need and have it all done I would need to delete "all" the files I have on the cloud so I can work on another folder? and it would remove those files from LR so it would not try to upload them again? Please remember I have over 500g of photos and only 20g cloud.
If it didn't try to upload to cloud I could just import all the photos and use LR to do all the organization and save them in their own folders saving me a lot of time
I don't mean to reply to my own post but I may of found the answer being new to LR I only considered that the newest LR CC would be the one to work with as the latest and greatest.
With the first video that 99jon recommended "importing files into lightroom cc" started off with an info on the 2 different versions of LR.
It would seem that I need to download and use "Adobe Photoshop Lightroom CLASSIC CC" as it is more of a file to folder based workflow and would not upload to the cloud
I have not validated this as of yet that it will do what I want but so far from what I have seen I would believe that it will
You might be better using Lightroom Classic. You simply choose what photos go to the cloud from Collections (Albums). Lr Classic sends smart previews to the cloud (smaller than originals) so 20GB of storage will go much further. Alternatively LRCC (without Photoshop) comes with 1TB of storage.