Q:

Would "Puff Daddy" sue if I call my social media thing "Puff"?

thank you for reading!
I want to name something after part of a rapper name. So that I don't give away the name, I will use "Puff Daddy" as an example and I want my product to be "Puff" as an example which actually stands for something meaningful and the acronym is respected in the digital field.
"Puff Daddy" the example rapper.
"Puff" as my example digital social media software and social media site. 
Puff Daddy is relatively unknown by me (chicagoland) but has 100s of thousands facebook followers. He has a mobile app so you know when his concerts are named "Puff Mobile". And he has a small TV series which might be discontinued but I'm not sure. He is still active and will be for about another 10 years I suspect. 
I am making a digital presence software which will also have a social media site created as a result. I will name it "Puff". No one else is taking this name space, except for "Puff Daddy". "Puff Daddy" also happens to have a trademark on the name "Puff Daddy", but not "Puff". His trademark has mentions of music as well as "multimedia", this is the only debacle I have. Importantly... His followers call him "Puff" even though he is constantly marketed as "Puff Daddy". 
My question, will he have good legal ground to sue my company social media site and social media software (does automation stuff)? Let's assume my business will do very well. Second, could I get a trademark on Puff having it state "automation, software, social media, etc." with no mention of music, but I would likely have to mention multimedia (I would change it to this in the future once it gets bigger). 
Second, if the name was 9-10/10, would you go with it in this scenario from what it stated? Or try to come up with a new name? 
Thank you! I really appreciate it!
The Names are as Examples, but extremely relevant

A:

The most important fact to bear in mind is that there's no way to predict whether a given individual will decide to file a suit against you, though we might say on what basis he might, if he so chooses. There are two basic grounds for a suit, one pertaining to trademarks and the other pertaining to use of names – misappropriation and violating the right of publicity.
A word can be a trademark, but the scope of protection is somewhat narrow because the protection is in terms of use within a given business. So calling your computer company "Apple" is out, but calling you roofing service the same is okay (assuming that somebody didn't previously register "Apple Roofing"). The main consideration is the likelihood of confusion. Supposing your business were selling landline telephones and I don't think Apple computer company sells such phones, you might still be in trouble if you called your company "Apple Phone", since they certainly do sell phones.
There are thousands of trademarks that include "Puff", including Cocopuffs and various pizza and cheese puffs. Since "Puff" is such a generic word, there is a higher bar to proving infringement (there are thousands of trademarks including "Puff"). "Puff Daddy" is, however, a registered trademark covering perfume, jewelry, clothing and certain online services, so there is a non-negligible chance of confusion.
In the case of names (or apparent names), an additional concern is whether this is commercial exploitation without consent of a person's name (which causes harm to the subject). The underpinning of this tort is that such a use falsely implies an endorsement of the product. Again, with a fairly generic word like Puff, there isn't a clear implication that Sean Combs has endorsed a product that is called "Puff Communications", but "Puff Daddy Communications" would almost certainly cross that line.
The main issues, then, are the extent to which the name is generic vs. unique, and whether it is likely that a person would interpret the product or service as being the same as another, or would constitute an endorsement. 

