How should you approach your adviser and tell him that he has a communication problem (Not his actual hand writing)



I am currently working under an academic research adviser who is a very nice person and very knowledgeable but I think he has problem in communicating with others (myself included) that is hindering the research progress and outputs of his group. 

This problem is demonstrated on three fronts:

1. Poor handwriting 

His hand writing is very very messy, comparable to the figure above. I do not understand how anyone can understand him. Everyone else in the research group communicates using Latex or some other software to make the writing neat and understandable. Further, he never erases anything but just scratches things out. Can you imagine what scratches on messy hand writing look like? Even messier.  

I'd like to think that messy hand writing is linked with unfettered intellectual creativity but I just cannot understand anything that he writes and neither can anybody else. 

2. Unclear presentation or slides. 

In my opinion slides should be made to the point, clear and concise. I found a random example not even related to my field of study to clarify what I mean: http://www.nobelprize.org/nobel_prizes/economic-sciences/laureates/2011/sargent-lecture_slides.pdf 

But his slides are routinely overloaded with equations and unclear graphics obviously cropped and pasted with no regard to background, positioning or anything. Simply put, the slides do not capture the main idea. And because of this reason he routinely go over time or skip large chunk of complicated equations during presentation, this causes 1/2 of the people to stop following him and it is very noticeable.

3. Unclear notation

I think this one is quite serious because he routinely uses symbols that are a little ambiguous in their meanings. In fact his symbols seems to consistently go against whatever is currently in the literature. For example, people in my research field uses Greek alphabets for one thing but he uses it for something completely different. Also there are definitions he sort of made up on the spot that I thought were standard. I am honestly not sure whether I should just adopt his conventions or keep whatever other people have been using in this field.

I think part of the reason is because he is from an older generation who is used to the paper and pencil type of work and is not very adapt with technology. I think he is also a very busy person so he has to come up with ideas and notations on the spot which causes conflict with the rest of the world. 

Is there a good way I can approach him to address these problems without offending him or hurt his feelings?
I would advise you to approach him on a different base than he has a communication problem, namely on the base that you have a problem with his way of communication. Note the slight shift.

Phrasing it that way eliminates the problem that you may accuse him of something or even offend him. For example, you would not say "your handwriting is poor" but "I have a hard time to read your handwriting and it costs me a lot of time to read it". Also, you would not say "your slides are unclear" but "I do not get the main idea from the slides and would find it helpful if [...]". Finally, instead of "your notation is unclear" you would say that "I consistently get confused since the book X uses the notation Y while you use Z".