$deletedFiles = @(git ls-files --deleted)
if($deletedFiles.length -ne 0) {
    $deletedFiles | % { git rm $_ }
    git commit -m "Deleted some files"
}

$f = git status --porcelain=v1 -u
if(!$?) { throw "Failed." }

$f = $f | % { $_ -replace '^...', '' -replace '^"', '' -replace '"$', '' }
$f = $f | % { ls -Force -LiteralPath $_ } | sort FullName

function BuildCommands($batch) {
    @($batch) | % {
        git add $_
    }
    git commit -m 'Adding new batch'
    git push
    if(!$?) {
        throw "Failed to push batch."
    }
}

$maxSize = 500MB
$totalSize = 0
$thisBatch = New-Object System.Collections.ArrayList
$commands = for($i = 0; $i -ne $f.length; ++$i) {
    $current = $f[$i]
    Write-Host $current.FullName
    $currentSize = $current.Length
    $sizeIncludingThis = $totalSize + $currentSize
    if($sizeIncludingThis -le $maxSize) {
        $thisBatch.Add($current) | Out-Null
        $totalSize = $sizeIncludingThis
        if($i -eq $f.length - 1) {
            # this is the final batch of stragglers
            BuildCommands $thisBatch
        }
    } else {
        if($thisBatch.Count -ne 0) {
            BuildCommands $thisBatch
        }
        $thisBatch = New-Object System.Collections.ArrayList
        $thisBatch.Add($current) | Out-Null
        $totalSize = $currentSize
    }
}