Solution 1:

I tried the hotkeys you listed... they worked fine for me and repeated automatically just fine when held down...

#Persistent
Return

#IfWinActive    ; Make replacement operate globally
RShift::Up
Up::RShift

You may be able to try a different SendMode...

RShift::SendInput {Up}
Up::SendInput {RShift}

or...

RShift::SendPlay {Up}
Up::SendPlay {RShift}

Do you have any other programs that are intercepting these or anything like that? Does the key repeat work normally when the script isn't running?

Setting up a custom loop might look something like this...

RShift::
    While GetKeyState("RShift", "P") {
        Send {Up}
        Sleep 50    ; Set delay to taste
    }
Return

EDIT

To address the need for other modifiers to work, a '*' may be used with the hotkey, although in the case of having two shift keys it may not work correctly by default. I've added a special case for the shift key detection but I don't know how that would work if you were to throw other modifiers into the mix... in that case you could look at adding the {blind} modifier to the Send statements to see if you could get it to work properly.

To address the 'race condition' another pre-repeat delay can also be added before the repeat loop along with an initial send statement (see below).

*Up::SendInput {blind}{RShift Down}
*Up Up::SendInput {blind}{RShift Up}

*RShift::
    Send % GetKeyState("LShift", "P") ? "+{Up}" : "{Up}"
    Sleep 250           ; Initial delay before repeat
    While GetKeyState("RShift", "P") {
        Send % GetKeyState("LShift", "P") ? "+{Up}" : "{Up}"
        Sleep 100    ; Repeat delay
    }
Return

Solution 2:

The problem with all of the other answers is that repeated shift presses will be ignored because the previous hotkey subroutine is still being executed. By defualt, #MaxThreadsPerHotkey is 1, and #MaxThreads is 10.

Below are two possible solutions. Both works well for me.

Increase #MaxThreadsPerHotkey (and #MaxThreads)

SendMode Input
#MaxThreads 150
#MaxThreadsPerHotkey 150

; return the send command including any pressed modifier keys
getSendCommand() {
    sendCmd = {Up}
    sendCmd = % GetKeyState("LAlt", "P") ? "!" . sendCmd : sendCmd
    sendCmd = % GetKeyState("LCtrl", "P") ? "^" . sendCmd : sendCmd
    sendCmd = % GetKeyState("LShift", "P") ? "+" . sendCmd : sendCmd
    sendCmd = % GetKeyState("Win", "P") ? "#" . sendCmd : sendCmd
    return sendCmd
}

*$RShift::
    ; Immediately send an up key
    Send % getSendCommand()
    Sleep, 450

    While GetKeyState("RShift", "P") {  ; while key remains pressed
        Send % getSendCommand()  ; keep sending up keys
        Sleep, 30
    }
    Return

Immediately abort execution when shift key is released

SendMode Input

; return the send command including any pressed modifier keys
getSendCommand() {
    sendCmd = {Up}
    sendCmd = % GetKeyState("LAlt", "P") ? "!" . sendCmd : sendCmd
    sendCmd = % GetKeyState("LCtrl", "P") ? "^" . sendCmd : sendCmd
    sendCmd = % GetKeyState("LShift", "P") ? "+" . sendCmd : sendCmd
    sendCmd = % GetKeyState("Win", "P") ? "#" . sendCmd : sendCmd
    return sendCmd
}

*$RShift::
    ; Immediately send an up key
    Send % getSendCommand()

    ; Initial wait period (sleep time = 350 ms, execution time ~450 ms)
    Loop 35 {  ; Check keystate every 10 ms, abort execution as soon as shift is released
        Sleep, 10  ; 10 ms is the shortest possible sleep interval
        if not GetKeyState("RShift", "P") {
            return
        }
    }

    ; Start repeating if and while key is still pressed. Stop execution as soon as shift is released
    While GetKeyState("RShift", "P") {
        Send % getSendCommand()

        Loop 2 {
            if not GetKeyState("RShift", "P") {
                return
            }
            Sleep, 10
        }
    }
    Return