re: Those with individual stocks - some general questions for you....

I do have an Ameritrade account that I "play" with. I own about 15-20 positions at any given time. Mostly large cap stocks I hold long term. Some that I may hold less.

You are correct that under a year is taxed much higher so it makes a lot of sense to hold for a year if you can. Ameritrade prints all tax documentation. I use turbotax and it uploads directly into the program so it's super easy to do taxes with it.

You can buy stocks, mutual funds, or ETFs very efficiently. You can utilize options and such but it seems that you likely wouldn't be interested in that.