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This is quite an extensive list where only a small subset actually will be done.
Do an OpenBSD dependency graph. Maybe in Haskell. Compare with FreeBSD’s portdepends.
3G failover over 3G. See e.g. ifstated.conf for failover
Port despotify to OpenBSD.
Try YubiKey - OpenBSD port available.
Fantastical like command line tool for entering events and tasks in google calendar.
Try tiling WM as ScrotWM
Setup a movida HTPC based on OpenBSD 4.7
Check out Ryan Freeman game ports
Install or develop a web-album on Photos.
WordGrinder - Create a port for WordGrinder.
HBench - Create a port for HBench
Port pinta - needs mono and GTK+.
Install gThumb - Great image/video/audio viewer editor.
Install Krita - Painting software part of KDE.
Port OpenSLP - similar to zeroconf and UPnP.
Port MyPaint to OpenBSD.
Port http://en.wikipedia.org/wiki/Varnish_(software). Good architecture for performance as well.
Secure distributed safe data storage. Use rsync, bittorrent or similar to distribute storage among friends or completely anonymous to a network. Avoid a single vendor and get control. See FreedomBox and OpenStorage.
Twyne - Make a interactive fiction game