Topic: Considering restart a Gen 1/2 Pokemon file, questions before I do

After playing Leaf Green recently I got the urge to replay the original Gen 1 and possibly Gen 2 games again, specifically Yellow version on the 3DS. The only thing is I completed all 6 versions on both Gen 1 and 2 on 3DS so will have to start a new file. Have a few questions:

1. I don’t have Pokemon Bank downloaded but my friend does, can specific Pokemon be selected to transfer to the Bank on friend’s 3DS and then transfer to my Gen 7 games from there?
2. If I want to bring my Pokedex quickly back to where I am on my current file that I am considering to restart, is the best way to transfer all the difficult to catch Pokemon into another version then transfer back to my new file?
3. Can the items and money I currently have be transferred/ salvaged if I restart a file? My guess on that is no.

I would appreciate any feedback on this. I was going to wait and see if Nintendo will re-release Gen 1 and 2 on the Switch so I don’t have to delete my file if I want to replay the games, but it looks unlikely now that they re-released the remake of Gen 1.

1. What you can do is manually trade your Pokémon with your friend (PS: he has the classic games on his 3DS)? And he also needs to have the Transporter. After that, he can transfer them to the Bank, and then transfer them to one of your Gen 7 games (your game has to be physical, obviously).

2. If you're going to start the game from scratch, I don't see the point in doing this. The most difficult Pokémon to catch are the dogs of Johto, but you can do it again without problems.

3. No.

If you want to get your pokemon back in your gen 1/2 games, then you’d need to trade them with your friend and then trade them all back.

Without having them enter Bank.

Thinking about it, it doesn't make a difference if the Gen 7 game is yours or your friend's (they only serve to remove Pokémon from the Transporter and transfer them to the Bank).
After that, transfer it to your Home.

@Rodolfo6493
Thank you for the info. My friend does have the 3DS gen 1 and 2 games. I know I want to save a few Pokemon from the Safari Zone, I remember some appear infrequently and are difficult to catch, also will probably save my Porygon.

@Eel
Thank you for your response. Will transfer out the rarest and most difficult Pokemon to catch, and possibly a few higher leveled ones before I restart the file. I wish the game has more than one save file but I understand why they only have one file.

You could also just mod your 3DS and download Pokemon Bank from the hShop (it's a free app, so it can't hurt). Modding a 3DS is pretty easy, so it shouldn't trouble you too much. This way you don't need to rely on your friend whenever you want to use Bank.