Anyone know how I can transfer items from my main island to my Dream Project island on my other, older switch? I can't seem to play both at the same time, and I don't know how to 'friend' my other character so I can mail stuff.
I assume you can't play both at the same time because you have a digital copy. If you have a 2nd profile that also has NSO, you can play together at the same time. Unfortunately, you can't befriend your other character without having played together, IIRC, so if playing online doesn't work, you'll have to find another way to transfer the items, such as borrowing a physical copy from someone, or having someone hold your items for you.
Coming from me who just got a second switch here's what you need to know. If you wanted to play Local with yourself you need to make sure you have 2 accounts that have 2 copies of the game digital or physical. However, if you own the game and the other user on the other switch doesn't own it, it will not be able to work. There is a way to play the game but this only works on a digital copy let me explain because this is going to sound complicated.
In order to play the digital copy of New Horizons you need to deregister the main switch and then use the 2nd switch and sign in using the main user from your 1st Switch that owns the digital copy of ACNH. You have to redownload the software in order for the 2nd switch to play the game. Now here comes the tricky part, if you try to use a user that doesn't own the game it doesn't let you play it because you don't own the game. The way to get around this is to make a 2nd account, and create a 2nd online membership in order to play online.
For me the only way I got mine to work was that I had another user on the main switch that have save data since they played the game. So what I did was I deregistered my main console, signed in with my main user who owns the game on the 2nd switch, then I let the other user play the game because they have save data they are allowed to play it despite the fact that they don't own it. So now I can use that user on my main switch to visit myself, by using online play. It does work from what I tested. I know this may sound complicated and confusing, trust me it is, but so far this method I just did does work. If you're still confused you can ask me a question and I can try to clarify.