Generally there won't be bugs or snow in Oregon in September, although that's starting to get late in the season. Be prepared for a week of steady rain and low 40's, upper 30's....or sunny and warm during the day and sub freezing at night, or even some snow, that time of year.
Ask the boss for a sabbatical. I did, and got it when I thru hiked. Thru hiking sealed for me the fact that I wanted to retire early, so I could do stuff like that any time I wanted.
Oregon is a good choice for a long section - it's flat and easy, by PCT standards. On a thru, you spend 2.5-3.5 months and it is nothing but California, California, California.....then you blink and you're thru Oregon in 2.5-3.5 weeks. Then you get your @$$ kicked by Washington since you'd forgot was steep climbs were like (Fire Creek Pass and up out of Milk Creek, to name two on the Glacier Peak section of Washington).