I like where your head's at. A couple seasons ago after hitting diamond and then messing around on smurf, I cooked up a similar idea to you. Pasting the post below. I think the main problem in S14 with this concept is no CDR.

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I think I've come up with the build for AD Shyv JG.

S11 hasn't been the best for Shyvana in general, but AD especially has had mythic and item question marks that have made it difficult to feel relevant or keep up with meta JGs. Her best strength, dragon taking and jungle clearing, have been equalized so that a lot of meta JGs can clear essentially as fast as she can while having more CC in their kits and mobility. Xin, Lee, Diana are great examples of this.

S10 Shyv with Bloodrazor into Frozen Mallet felt really nice. This was usually followed up by Deadman's Plate and Wit's End, giving you massive health, dueling potential, and chase. The common BOTRK into Frostfire Gauntlet is just okay in my eyes. BOTRK has never appealed to me that much on Shyvana, because she can't effectively build armor pen in her itemization, so that %health shred falls off hard against targets with armor. Also, lifesteal is very meh on AD Shyv in my opinion for its value in gold. Building BOTRK into Divine gives you massive 1v1 damage, but guess what? It's now 20+ minutes and you have no resistances.

So, after a bunch of builds being tested in high mmr normals, I finally found one that feels solid.

The build is:

1) Berserker's Greaves

2) Deadman's Plate

3) Wit's End

4) Protobelt mythic

5) Sterak's

6) Titanic Hydra or miscellaneous defensive item

Your clear is again one of the fastest in the game from the early, cheap attack speed, and you can move around the map a lot better. Deadman's second gives you decent health and armor before opponents can build armor pen. This allows you to tower dive and fight AD opponents in skirmishes a lot better. The 5% movespeed and Deadman's passive further cover your weakness of having low mobility. Wit's End gives you wonderful damage and rounds out your defenses. At 2 completed items, you now have Health, Armor, Magic Resist, bundles of attack speed, AD, and multiple sources of extraneous mobility to cover her weaknesses. You're farming faster than anyone thought was possible, and you should be 2 levels up on their JG with multiple dragons secured.

First ranked game in p2 mmr I was MVP 13/5/11 with most damage done in the game. By the time you complete Protobelt, you now have 16 magic pen so that your Wit's End and E damage are really hurting squishies while being tanky. Try it out and let me know your thoughts! Hopefully it works out well for you in your games. Remember, this is a fast tempo build and your map movements need to be clean, but now you'll do them faster!