It is hard to ignore the itch to shave. Just do it.
From my own experience if you're having the thought about shaving then you have probably lost at least a little confidence with your current appearance. From the pics it's clear you are well on your way to naturally balding. There will be no harm in giving it a try. You can always grow it back if you're not ready to be completely bald. Though I haven't met a bald guy yet that is itching to grow his hair back or wishes he wasn't naturally bald. It's an amazing feeling to be bald. I say go for it and give the 30 day rule a try.
Well, you are almost bald right now. the visual appearance will be almost the same. Go for it.
You'll look fine. And you will enjoy the nice feel of a freshly shaved head. That is the real selling point for me. A co-working is sporting a pohawk (polish mohawk -- he likes to joke about the ethnicity). He says he loves the smooth feels of the shaved sides. Seriously thinking of going sly like I have done.
Yes, anytime is a good time. Go for it.
The right time is now. Like some others have said, don't waste any more time in limbo. Your life is happening now. Liberate yourself from the burden of thinning hair and receding hairlines.
Give it a try. If you don't like it,it will grow back. But you will like your smooth head