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I use my Tanaka/Nils sparingly the last 5 seasons since I got an Ion, but a couple years ago it was hard to start. Took it to a guy who repairs them, he replaced the fuel line and primer bulb and it was good to go. Yours sounds a little different, but thought I'd throw it out there. A little Seafoam wouldn't hurt in case there's a little varnish in there. Best of luck with it.
I have two Tanaka's, best move I ever made, until I got the Clam Plate & Milwaukee Fuel drill. Both Tanaka's were hard to start from the beginning. We (BEE, Blueberryman, C. Tripp & I ) modified the carburetors by removing the plastic plug over the idle screw, so we could increase the gas flow. You have to heat a needle & push down on the plug, let it cool for a second, then pull it out & increase the flow. That solved the problem. Apparently they set them at the factory for the warmer Southern states and put the plug in to get us to go to a shop for service, if we have problems That motor is mainly used as a bulb planter.
Some of the things others have mentioned may solve your problem. But in the meantime be VERY aware that starting fluid in a 2cycle engine spells "early death" as it washes all the lubricant of all moving parts.
What auger do you use withthe Milwaukee ?
been hesitant to do that yet, i remember your post to press a hot finish nail into that section. this one has been pretty easy to start til middle of last year. going to change the plug as others have mentioned though it still looks fine. if that doesnt work ill do the hot nail trick. should probably buy a clam polate in case they stop making them someday
ethanol is the big problem. If they only knew how much gas had been dumped into the ground they would stop buying the junk Iowa need to grow food not fuel!!!!!!!!!!!!!!