With Cygwin, once you have all pre-requisites Transmission (libtransmission, daemon and transmission-remote which is what I use) builds out of the box.
In the pre-requisites you'll find almost everything available with Cygwin's installer (setup.exe), the only thing I have to build myself is libevent (which also builds out of the box, latest version 1.4.14b) and you have to tell Transmission's configure where it is, I use:
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./configure --disable-nls --disable-cli --enable-daemon LDFLAGS=-L/usr/local/lib
You, of course have to take out that --disable-cli, don't need the --enable-daemon, and make sure you have installed curses (ncurses actually).
I also build my own curl, since Cygwin is always behind in versions, but that probably is not necessary.
If you want to investigate what went wrong with file association and since you're also a developer... take a look at your registry, is any file association different of, for instance, if I dump the changes my installer does for .torrent files:
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Windows Registry Editor Version 5.00
[HKEY_CLASSES_ROOT\.torrent]
@="TORRENT file"
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Windows Registry Editor Version 5.00
[HKEY_CLASSES_ROOT\TORRENT file]
@="TORRENT file"
[HKEY_CLASSES_ROOT\TORRENT file\DefaultIcon]
@="C:\\Program Files\\Transmission-Qt\\transmission-qt.exe,0"
[HKEY_CLASSES_ROOT\TORRENT file\Shell]
[HKEY_CLASSES_ROOT\TORRENT file\Shell\Open]
[HKEY_CLASSES_ROOT\TORRENT file\Shell\Open\command]
@="C:\\Program Files\\Transmission-Qt\\transmission-qt.exe \"%1\""