Yeah Chilli..... I would go with the 19 " front even with the leading front axle like on our older bikes. That 120 x 18 rear tire you put on there is good . Not only is it wider then the 110 x 18 tire that WAS on there... but it is also going to be taller. It will be very close to the 90/90/19 that you are likely to put on that front wheel. The bike will sit nice and level. You MAY want to get 1/2" LONGER then stock, rear shocks as well. Set your sag to about 3/4-1". The slightly taller ass end will shift your weight more forward on the bike... this will stabilize things and make the two separate frames of the bike... the front end , and everything on the rider side of the steering stem more stiff. Lower Handlebars help here too. The bike will handle great in the corners and twisties AND in a straight like Blasting down the highway. And use those lower tire pressures on that Enfield. I don't care what any body else tells you. I thought it myself and have been through it. 8 years of beating on this bike tells me so.
Drain that sorry excuse for fork oil out of those front legs. And put in 265 Ml of real fork oil... 15 or 20 weight. Use 10 or lower weight if you want it to ride like a sponge .
You wanna get real crazy ? ... stiffen the swing arm with a cross brace, an arch brace or a trellis brace . Loose that massive rear end with it's heavy ass fender and stays that tie into the main frame ? And OMG !.... will you have a nice handling bike !
You CAN have the bike running nice and stable in it's stock form now, with the stock motor. Right up to the maximum speed that a stock motor can put out... without any money, but just a little time and chassis checking. But, your doing that motor work like I did ? Your gonna want it stable right up to that ton and beyond like you are shooting for.
When you have that motor out of the bike and it's all taken apart.... Check the frame tubing for anything that is not square. Check you all your motor mounts and corresponding holes in the motor. Make sure that the motor sits in there snugly and squarely with out any stress. You shouldn't have to force anything in. Modify those motor mounts if you need to. That is where a LOT of the problems with vibs and cracked frames on these bike come from I believe. Get it right and your bike will be SO much better if you are having a problem with it.... What blue loctite ?!