98 GRIZZLY WON’T START

Okay I am brand new to the forum. Let me start with how I got here. I live out in the counrty in upstate new york with a driveway of 350′ in which the grizzly has handled in the winter months no problem. How did I get the grizzly.Well after looking locally I found it in the classifieds. Siiting in someones back yard 4-5" in the ground no papers,air box full of water,but only 150 hours on her. That was four years ago. Anyway cleaned carb,full srvice done and she went off and has not stopped not even a little.Has even started in low temps no choke all the time. Well it is winter now and a week ago I went out to start her to plow and it would turn over and just kinda pop almost wanting to.so I removed carb cleaned it out through in new ngk and she went right off again like a bear.tried it couple nights in a row just to keep checking and no problems. I did however notice prior to first carb removal some gas on case. So went out couple days ago and same thing gas on case which had been dry. After looking closer carb is not seated all the way forward in boot so I am thinking gas was coming down front boot and that was the leak.so when I did this it comes out of rear boot at least 1/8" gap. I need this machine as it does what we need and more so hopefully you guys can help. I know it is a small problem just want to diagnose correctly and no rabbit trails they can be costly. so here are my questions.
1. If the carb is not fully in boots will it not run and just pop like it wants to?
2. I am correct in thinking that is my leak,fuel running out of front boot down carb to cases?
3. Do the boots get dried over time and get shorter.It is 19 years old all original.
4. Where do I go from here? new boots or just one?
thanks for any help with the beast.