This thread was originally about whether you'd need a heatshield as well as a good thermally insulated spacesuit for emergency re-entry. You've been saying a heatshield is not necessary if you're plunging straight downwards a la Kittinger. But, you are using altitudes well into outer space as examples. Even if we allow for a vertical plunge rather than the usual shallower re-entry angle - even then you're still not making sense.

Kittinger jumped from the upper reaches of the atmosphere, not from outer space. As you point out yourself, he would reach terminal velocity. The speed of an astronaut, starting his 'vertical jump' from outer space would be much greater by the time he hits the outer reaches of the atmosphere.

What do you think would be the heat effects (not even to mention the shock effects) of someone hitting the upper atmosphere at thousands of miles per hour. What possible difference can it make that the descent was straight vertical instead of the usual profile? Why should there now be no significant heat effects?

The Golden Gate Bridge roadway is 67 meters above water. Someone jumping off that, reaches a velocity (neglecting air resistance) of √(2*9.8*67) = about 36 meters/second. That's enough to kill them.

The upper atmosphere has nowhere near the density of water, but to someone hitting it at extreme velocity (as you point out unhindered by air resistance) - it will present to him, the density of something like concrete I would imagine. What do you think would happen to him? Are you assuming some magical shock absorbers built into his spacesuit?

This is not meant to be personal Tom, but there are just 2 ways I can think of to get back from orbit:

1) heatshields, whether personalized or not;

2) some kind of controlled, powered descent.