If it makes you feel any better, I'm doing the same thing with my 2 1/2 year old. It wasn't intentional, it just happened and became the norm. I get criticism from my mother in law about it, but it works for us for now.
One thing that helps is a crib tent. It attaches to the top of his crib and he can stand up in it and still be contained. I did have to attach a bungee cord to the zipper so that he can't open it by himself.
My son has been in daycare for more than a year and easily goes down for a nap by himself. It took a few days for him to adjust, but it wasn't a struggle. He can do it, I think it's me who isn't ready to do it.
Anyway, know that you aren't alone. I wish you luck with whatever you choose to do.