As I've been called out before- I'm quite a newbie when it comes to towing. I can't tell you what difference he'll feel or if it'll be "better" (I know that one gets OldCoot's goat- ie, what defines "better"). But- I can safely say, we have a single car garage on the smaller side (suburban living at its finest) and my truck is too tall, too wide and too long to fit in. Not that I'd actually get the garage, it sucks not being able to pull it in to tinker or install/remove the hitch. However, you said it has 9' doors- it'll be cozy but doable. He just has to be mindful coming in/going out.
As for convenience of around town driving- there are extra hassles as expected. I have about 23,000 miles on the truck and have had it since May 2012 but only 5,000-6,000 of those miles are towing miles (maybe more, but a majority of my driving is non-towing). I'm blessed to not have a daily commute.
In that driving, I've done most of things people say you can't do - drive thrus (here, length is more the issue- I've ridden up and over curbs because of it and try to avoid the tight ones; you learn which are truck friendly and which aren't), drive up ATMs (height is more of an issue than width), close parking (did malls and shopping centers for Christmas shopping BUT I prefer far away parking spots- someone hit my rear driver's side dual and didn't leave a note
) and have driven it in Baltimore city (haven't done DC), I even took it into a parking garage in Baltimore with a circular entry (don't want to do it again, but I pulled it off. We used to regularly take it to women's lacrosse games at Hopkins. I've had it in beach towns with the tight parking required there (and no way to get away from it). Even used it for all of the major tourist trap attractions in Orlando and everywhere between.
I cannot take it to any automatic car wash around here. Though, there used to be a guy at the gas station who would wash and vacuum it for $40. Sadly, "Prince" took over and now he wants $80 at a minimum but does more detailing.
I've parallel parked it once- POORLY. Not sure what happened there. It was a huge spot.
Even though I did it all above- a lot of stereotypes are true. I prefer parking further out to avoid my fellow idiots who hit things (both my vehicles are victims of hits right now
). I prefer to avoid most drive thrus (belly appreciates it, too). For city driving- I prefer my car over the truck. It's doable, but jus takes some extra care.
For me, the dually gives me the most stable platform for towing my 40'+ and 14k+ and honestly I can't imagine towing it with less (anyone, really but specifically *ME*). Having the extra "oomph" possibly saved me from me when I wholly botched my parking at a campground. The negatives above are overtaken by what I feel like is the right truck for me/the job at hand- I wanted a big camper, a big truck was required.