Ditto on Tom's comments; if you have trouble installing a tubed tire, you reeeaaly won't like trying to re-seat a tubeless tire on a rim in the field. Spoked wheels are used on every real dirt bike and all dirt oriented dual sport/dual purpose and ADV bikes for good reason. While you can convert a tube type spoked wheel to a tube-less setup, the issues dealing with re-seating and maintaining the seal make it a poor idea IMO.
Tubes are simple and easy; while it isn't my favorite task, it gets pretty easy after the first 100 or so! LOL....all technique as Tom said.
The Tubliss system may be the best of both worlds but it isn't recommended for highway use and they don't make them in 17".......which is why I just purchased two 18" Excel rims, spoke kits and hubs to make my own KLR Tubliss setup.