The original install failed with the status code STATUS_DLL_NOT_FOUND (0xC0000135), as reported in "Python 3.5.3 (32-bit)_20170217102132_008_pip_JustForMe.log":

    MSI (s) (88:D8) [10:22:59:574]: Executing op: ActionStart(Name=UpdatePip,,)
    MSI (s) (88:D8) [10:22:59:575]: Executing op: CustomActionSchedule(
        Action=UpdatePip,ActionType=1089, Source=BinaryData,Target=CAQuietExec,
        CustomActionData="C:\Python\Python35-32\python.exe" -E -s -m ensurepip -U --default-pip)
    MSI (s) (88:C4) [10:22:59:588]: Invoking remote custom action.
        DLL: C:\Windows\Installer\MSI2C60.tmp,
        Entrypoint: CAQuietExec
    MSI (s) (88:B0) [10:22:59:588]: Generating random cookie.
    MSI (s) (88:B0) [10:22:59:590]: Created Custom Action Server with PID 6212 (0x1844).
    MSI (s) (88:A8) [10:22:59:630]: Running as a service.
    MSI (s) (88:A8) [10:22:59:631]: Hello, I'm your 32bit Impersonated custom action server.
    CAQuietExec:  Error 0xc0000135: Command line returned an error.
    CAQuietExec:  Error 0xc0000135: QuietExec Failed
    CAQuietExec:  Error 0xc0000135: Failed in ExecCommon method
    MSI (s) (88:D8) [10:22:59:658]: Executing op: End(Checksum=0,
        ProgressTotalHDWord=0,ProgressTotalLDWord=287056)
        CustomAction UpdatePip returned actual error code 1603 but will be
        translated to success due to continue marking

Did your system require a reboot for Python 3.5 to work?

From what I can see in "Python 3.5.3 (32-bit)_20170217131555_007_pip_JustForMe.log", it looks like the repair skipped installing pip. 

    MSI (s) (D8:1C) [13:16:31:822]: Skipping action: SetRemovePipCommandLine (condition is false)
    MSI (s) (D8:1C) [13:16:31:822]: Skipping action: SetUpdatePipCommandLine (condition is false)
    MSI (s) (D8:1C) [13:16:31:822]: Skipping action: UpdatePip (condition is false)
    MSI (s) (D8:1C) [13:16:31:822]: Doing action: InstallFinalize
    MSI (s) (D8:1C) [13:16:31:822]: Note: 1: 2205 2:  3: ActionText 
    Action ended 13:16:31: PublishProduct. Return value 1.

Maybe Steve Dower can shed light on why a repair with pip selected didn't try to install pip.