In hindsight, its easy to see why Boris Yeltsin was elected President of Russia - after all, there was no history of election in the country. Still, Russia - and the former Soviet bloc as a whole - was in such shambles that it would have been unlikely anyone would have done much better.
Without a doubt, Boris Yeltsin deserved to be elected to the Russian leadership after Communism fell. He was a capable leader with a proven track record, and there was no reason to deny him the helm of the country. Very few people could have taken the reigns, but he proved capable and more than ready.
Yes, Boris Yeltsin should have been the elected Russian leader after the fall of communism, because he at least wanted to take the country in the right direction. Gorbachev was even friendlier to the west, and arguably did more to advance Russia, but Yeltsin was far better than Putin is today.
I look at Boris Yeltsin the same way I do as tech startup visionaries. In both cases, you need someone at the top who has a burning passion for what your government or organization can do, someone committed to setting things on the right track. And he tried. Of course, the Russians screwed that up completely with Vladimir Putin, but oh well.
After the fall of communism, the Russia country was in a period of upheaval. There was so much change and chaos that the position would have been hard for anyone. I think that Boris Yeltsin did a decent job. Any person coming into that position would have had a very tough time.