First impression- two times too long. Places to cut down? Start with “who hasn’t been outside in years”; change to “agoraphobic”. Next, change “with his recently divorced next door neighbor, blah, blah, blah…” to “takes a road trip with his inspirational speaking neighbor”. Is the protag’s employment necessary in the logline? Loglines are prime real estate for words, so use as few as possible and say as much as you can with those words. Squeeze the last line in ith the rest, so it can read something like:

“A milquetoast agoraphobic takes a road trip with his newly-divorced, inspirational-speaking neighbor, who is secretly planning his/her own suicide.”

As a story, I find it compelling and intriguing, and would hope that it would have a comedic flair, although the genre is not clear in the logline. That’s my two cents- good luck, Matthew!