I'm at my most comfortable level musically when I pick and sing with my brother. The only problem is he lives about 1500 miles away from me, and that may soon grow to a bigger gap as he will relocate soon.
When we are together however, it's non-stop as we try to make up for lost time. He's a fine singer also, and likes the same types of music as me so it makes for some good sessions.
Generally, I play alone, but keep myself amid books and videos that are full of exercises, scales etc, and try to measure my progress in some way. I'd love to take some lessons from Rick but he lives about 400 miles away. Maybe I'll get up to Toronto someday as I hope to.
Clifton