So I'm far from an expert in this game but ive found a reliable method to fight the Mr Shakedown's and get the yen necessary to level up big time. Using this method is got 1 billion yen easy in about 1 hour.

Unfortunately I've only figured this out during a Majima chapter but I'm sure a similar strategy will work on the Kiryu Shakedown's too. I'll test it when I get to a Kiryu chapter and let you know. I'll also test all the difficulties to see if the strategy works. I've tested it on easy only so far.

First things first is you need the right equipment. Go to Don Quijote and buy and umbrella (300,000) and a selection of both health and heat drinks. I get by with 6 of the strong drinks that give you health and heat, and 4 of the strongest heat only drinks.

Now for the hardest part, finding them. In Osaka the first Shakedown tends to be prowling in the north east of the map, while the second prowls the western side. They tend to spawn at random. If anyone knows a reliable way of making them spawn let me know!

But know that one will spawn at a time, alternating everytime you win a fight against them. Once you find one try to find the nearest save so you don't lose him or your money if you lose!

For the fight itself the umbrellas heat move will easily destroy them. The main worry is defence and heat management. Your main damage will be through the umbrella so focus your attacks on building/sustaining heat by using the quick square square triangle combo or just triangle to stop your heat draining.

Use the thug style for fast hits and dodging and never use the umbrella as a plain hitting weapon they last much longer with just heat attacks as they only degrade 1 point per heat attack so only pull it out when you're ready to deal damage.

Defence is easy, stay close and quick on the block button, if you're close he'll tend to use two moves in his first (blue) phase.

One is a three hit combo (Although sometimes he only hits 1-2). The best way to deal with this is to block the first two and step back for the third, make sure to use his sound cues (or lack of) to know if he is finishing the combo and you can get in a quick attack, just don't over commit, patience is key. For the 1-2 attacks a quick triangle attack is good. Dodging the full 3 combo though will give you time for a square, square, triangle combo good for a quick heat boost.

The second attack is a big hit but just blocking it should be enough to not take damage and still get a few hits in. It's not hard to dodge though so try to get that down.

Then when you have enough heat use the umbrellas heat move to deal a large amount of damage. Try not to waste your heat drinks here you should be able to boost your heat through normal attacks. And make sure to keep your health topped up. If you make a mistake you'll need all the health to avoid an unnecessary one hit loss.

Once down to half health he'll go into the second (orange) phase. In this phase start to keep your distance so he'll use his two charge moves. One is a more powerful version of his blue charge, it'll break your block but cause no damage so if you can't dodge then just block. The second charge is more dangerous but easier to dodge too. He'll taunt before leaping at you, make sure you don't attack during his taunt and dodge the leap. Don't try to block as he'll go through it and probably one hit kill you.

Don't bother with normal attacks in this phase Id say just use the heat drinks to fuel your umbrella heat attacks to try and get through this phase as fast as possible all the while ensuring you dodge properly and take no damage.

And that should be that. After 1-2 fights you should get the timing down and it becomes almost trivial to take them down. Just remember to save before and after just in case. Invest in replacing any supplies and weapons then pump your abilities tree full of yen.

I hope this helps and I hope this wasn't a pointless waste of time that you all probably know already... And apologies for the layout/structure, I've written this on my phone.

Thanks for reading!