Though it is not hard to learn traditional Chinese from simplified or the other way around, I would prefer simplified over traditional Chinese due to the ease of recognition and writing. For sure, traditional Chinese does keep the meaning of the word within the character, but it contains unnecessary amount of strokes for current day usage. Simplified Chinese does not take away the meaning of the words, where scholars supporting traditional Chinese argues about. If you put the word in a sentence and you still don't understand the meaning, it does not matter if the word is simplified or traditional.
As for Mandarin, I would say standard Mandarin pronunciation is better than any dialect including Beijing. Even though there exist different dialect across China. A lot of migrant workers speaks "standard Mandarin" with a little bit or a lot of dialect, but it is understood by everyone that speaks Mandarin. The current generation of students in China are learning to speak standard Mandarin and most of the TV channels and shows use the standard pinyin pronunciation. I do not feel that standard Mandarin is a strip down version of any dialect.
The following may be offensive to Beijing Mandarin speakers. I used to work in a call center and had to use Mandarin on some of my calls. I have to learn from experience that Beijing Mandarin speakers pronounce the number 1 as "yao" instead of the pinyin "yi", which I myself pronounce it pronounce it "yi". One day I got fed up in "correcting myself" because the callers kept pretending to not understand me when I am using standard pronunciation, so I have to speak to them in English letting them and said: "I do apologize but my Mandarin is not good enough, I would need to speak with you in English. If you would prefer, I can transfer you to a proper Mandarin agent and they will be able to assist you" and right after I said that, they miracly understand the number 1 "yi"
What's the big deal? People say "yao" instead of "yi" over the phone so you don't confuse it with "qi" for seven. It's not like one is correct and the other isn't, no need to be so stuck up...
Also it's not only Beijing Mandarin speakers who say "yao," all Chinese people do. Sometimes they call zero "dong" instead of "ling," do you get all ruffled up about that too?
The dialect we call Mandarin originates from the three northeastern provinces, and the Standard Mandarin (Putonghua) we have today is simply a homogenized form of the Beijing Mandarin, or 官话 used during the Qing dynasty.
I don't think Beijing Mandarin is any harder to understand than your Putonghua, they are pretty much one and the same, except Putonghua lacks some of the colloquialisms and slang terms in Beijing Mandarin.
On the subject of Traditional vs. Simplified, I don't think it's a matter of personal preference but rather dependent on what you're used to. If you're from the mainland, you use Simplified, if you're from Taiwan/Hong Kong, you're used to the Traditional rendering. Using either rendering doesn't really change the way the words are used, so I don't see why it really matters unless you're trying to design something with an artistic or historic theme or something.
Regional dialects I think are much more interesting than any Traditional vs. Simplified contention, and the specialties and nuances of regional dialects are truly worth further study and preservation. For example, in many dialects like Cantonese and my own Hunanese, there are certain characters and figures of speech that have disappeared from Putonghua but are much closer to the Classical Chinese of ancient times. These characteristics represent a part of the Chinese heritage that is coming under increasing threat from Putonghua Standardization and its ubiquity in films and the media.
Plus you have to keep it clean as well and not let old ink stay in there for too long or else it will get all clogged up.