Its quite simple to do in windows.  Create a shortcut to the wallet .exe and add -rescan into the properties of the shortcut on the very first line.  Every time you click that shortcut it will run the command you entered on the end.   I think this is called a command line switch and there is a list given under help for other commands. 

I thought adding some coins was reasonable here as part of a positive trend.  Sent it from exchange, as always very fast but didnt trigger the correct balance to show just yet, it immediately accepts incoming and shows this months but not last months incoming or last years even which is the majority.   It did then say it was staking, weight etc however looking now its saying not mature so I presume its all linked to it being incorrectly aligned somehow.
I do have it setup right elsewhere as well however that wallet refuses to see any peers so its not live though it was previously and loads fine, correct but old info, etc.   I'll see if I can transfer the peers.dat across and jump start it

[I reposted the OSX compile bounty elsewhere, seems important]