Hey guys 
Typography was also a nightmare for me too. I can’t even count how many rejections i had in the past because of that! I hate to admit but it turned out that the reviewer was right! 
I had enough, so a month ago i spent days trying to understand and learn what makes a good typography!
So here are my tips:
Google fonts:
If you hover over the typeface (yes, there is a difference between a font and typeface! :-D) you will see an icon named “pop out”. Click on that and choose the third tab (Pairings). Voilá! Now you have more than 600 typefaces and you have at least 5 suggestions for pairing. In 99.9 % of the time it does the trick.
Lynda
I found this 3 video tutorials from Ina Saltz on lynda.com and it really changed my whole life! It’s not that long, ca. 4 hours but it’s worth every minute! It’s amazing how she explains everything!
And keep in mind, that guides and grids are your best friends when it comes to alignment!
I’m not saying that i became a professional after this but it really helped me a LOT!