Hello Barney... and welcome to the IP Yacht Owner's Association.
I have an IP40, hull #132 and after adding new electronics, solar , A/C, Anchor wash, and more, feel somewhat qualified to speak to your first question.
1. Although I have no experience with other boats, I was somewhat disappointed to not find a wiring chase to pull wire from bow to stern. I will not lay wire in the bilge which does run the entire length, so it can be a difficult pull through lockers and holes that are already bulging with existing cables. If you are doing a major overhaul, then holes can be made larger and possibly a chase installed, particularly in difficult to access areas. Fortunately, my wife is petite and she was able to get into areas I couldn't reach. I found plumbing to be very similar. From what I understand, IP builds the hull in courses, adding all wiring and plumbing as it goes up. Makes perfect sense for construction, but can be a pita when you need to make an addition. So, I would summarize the difficulty factor at a "6-7" out of 10...not impossible, but you will be talking to yourself at times.
2a. Berthing at the marina while short handed. I assume you mean docking the boat in a slip. Neither my wife nor I ever sailed before November 2009. We took three ASA classes and then practiced, practiced, practiced. Without a doubt, docking is the most tense activity I have encountered to date, (and the closest I came to an accident at St Marys, GA). So much depends on the layout and conditions of your marina. Fortunately our marina is quite sheltered and while it can be blowing 15 -20 mph on the Neuse River, It's only doing 7 while I'm pulling into the slip. If there are no strong currents or winds, docking an IP40, even in a restricted area, can be done with one or better yet, two people. The key for us is doing it SLOWLY! I'm coming in at a slow walk speed so corrections can be gentle and if necessary my wife could "push off" a piling or, heaven forbid, another boat. As you learn how prop walk affects your boat, that characteristic can be used to your advantage. (My boat prop walks to port in reverse)
2.b Our slip works best by pulling in stern first and then while exiting the slip prop walk pulls the boat in a gentle arc to port, setting me up to drive away.
From my limited experience, the IP40 is a wonderful boat. My wife and I both love Charbonneau as a dear friend and can't wait to get back to her in another three weeks.
Bill