Starting from TBC to TWW. Kind of half tempted to do it.
Each expansion will take 3-5 days, depending on your play time.
But I am pretty sure you will get burnt out. Go slowly.
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That’s really not too bad. Thank you!
You’ll get the Loremaster Achieve whilst you’re doing all those quests! Have fun. 
Kinda depends. Are you just doing a main quests or including side quests? Some of them are time gated like Legion profession quests.
I remember when cataclysm came out and I made this character. I wanted the loremaster title. it took me four months to clear all of the necessary achievements to get loremaster for just those four expansions. now we have dragon riding so it could go a little faster but if you’re talking 10 expansions even it two weeks solid each, you’re still looking at five months. these numbers, of course, are based on the idea that you’re only gonna play about 4 to 6 hours per day
I did Loremaster on two toons pre-Cata and I’ll just say take your time and go easy on yourself - it’s not going anywhere, and addons / guides these days will make a big difference.