TPath.HasValidPathChars is completely broken. This is its implementation:
class function TPath.HasValidPathChars(const Path: string;
  const UseWildcards: Boolean): Boolean;
var
  PPath: PChar;
  PathLen: Integer;
  Ch: Char;
  I: Integer;
begin
  // Result will become True if an invalid path char is found
{$IFDEF MSWINDOWS}
  I := GetPosAfterExtendedPrefix(Path) - 1;
{$ENDIF MSWINDOWS}
{$IFDEF POSIX}
  I := 0;
{$ENDIF POSIX}
  PPath := PChar(Path);
  PathLen := Length(Path);
  Result := False;
  while (not Result) and (i < PathLen) do
  begin
    Ch := PPath[i];
    if not IsValidPathChar(Ch) then
      if UseWildcards then
        if not IsPathWildcardChar(Ch) then
          Result := True
        else
          Inc(i)
      else
        Result := True
    else
      Inc(i);
  end;
  Result := not Result;
end;
The crucial point is the call to IsValidPathChar. Let's look at what that does.
class function TPath.IsValidPathChar(const AChar: Char): Boolean;
begin
  Result := not IsCharInOrderedArray(AChar, FInvalidPathChars);
end;
Now, FInvalidPathChars is defined to be:
FInvalidPathChars := TCharArray.Create(
  #0, #1, #2, #3, #4, #5, #6, #7, #8, #9, #10, #11, #12,
  #13, #14, #15, #16, #17, #18, #19, #20, #21, #22, #23, #24,
  #25, #26, #27, #28, #29, #30, #31,
  '"', '<', '>', '|');            // DO NOT LOCALIZE;
That is, all ordinals less than 32, and ", <, > and |.
We also need to understand what IsPathWildcardChar does.
class function TPath.IsPathWildcardChar(const AChar: Char): Boolean;
begin
  Result := IsCharInOrderedArray(AChar, FPathWildcardChars);
end;
Where FPathWildcardChars is:
FPathWildcardChars := TCharArray.Create('*', '/', ':', '?', '\'); // DO NOT LOCALIZE;
Now, back to TPath.HasValidPathChars. Let's consider this if statement:
if not IsValidPathChar(Ch) then
The condition not IsValidPathChar(Ch) evaluates to True when IsValidPathChar(Ch) is False. Which happens if Ch is in FInvalidPathChars. That is if Ch has ordinal less than 32, or is one of ", <, > and |.
Your test string is 'C:\test\test?\' and in fact none of these characters are in FInvalidPathChars. Which means that the condition in the if not IsValidPathChar(Ch) then statement always evaluates False. So even though your string contains a wildcard, it can never reach the subsequent test:
if UseWildcards then
It is easy to conclude that HasValidPathChars returns the same value irrespective of the value of the input parameter UseWildcards. And if you have any doubt about the analysis, this program should dispel it:
{$APPTYPE CONSOLE}
uses
  System.SysUtils,
  System.IOUtils;
procedure Main;
var
  Ch: Char;
begin
  for Ch := low(Ch) to high(Ch) do
    if TPath.HasValidPathChars(Ch, False)<>TPath.HasValidPathChars(Ch, True) then
      Writeln('different at #' + IntToStr(ord(Ch)));
  Writeln('finished');
end;
begin
  Main;
  Readln;
end.
This looks like yet another function in this dreaded IOUtils unit that has been improperly implemented and not tested.
I have submitted a bug report: RSP-18696.
Based on having stumbled upon many such problems with IOUtils, my experience is that the unit is not to be trusted. I would not use it. Find an alternative way to solve your problem.