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First of all, how do I know when I should use display inline-block, tables, floats or whatever else. How do I know which one is the correct for the current situation?

Unfortunately, the answer is experience.

The second question is… how do you determine whether you have to support IE9 and below or not?

If I’m creating my own project for my own use then I’ll decide what browsers I want to support based on the audience I’m trying to reach.

For my company, they’ll check their analytics to see what browsers are being used to visit their site(s) first…then decide, again, on who they are trying to reach.

I’ll still probably build with fallbacks for, perhaps, one older version than my target minimum but with the knowledge that those users won’t get the full experience.

It’s a balancing act…