I hope someone here knows about his stuff.

I just bought a 1998 Yamaha timberwolf 250 2wd. I brought it home last night and rode it around a little. Then this morning it was 38 degrees and I wanted to see how it did after sitting all night in cool weather. I had left it in neutral the night before. I turned the key on and the neutral light wouldn't come on and needless to say the electric start wouldn't work. I pulled the starter cord and with one little pull it started right up. Then after 2-3 seconds of running the neutral light came on. I drove around a little then switched it off then on again and the neutral light and electric starter worked fine.

Could this be a battery issue? The battery looks pretty old.

A new battery and ya should be good to go.

Yelp
you might see if it would charge and hold it before you buy one.

You could also have a voltage leak that pulls the battery down. If it's been totally discharged a few times, chances are that it's damaged and won't hold a full charge any more.

To test for a voltage leak, have the battery charged and pull off the + lead. Make sure the key is off. Put a voltage meter between the lead and the post. If it registers anything, you have a leak.
You can use a test light, too, but if the leak is very small, you won't have enough stray juice to light it.

It's not common, but on occasion, a very dirty battery will leak voltage because it's going through conductive grime.

Dick

Check if your connections are good on your battery. It looks like it's getting bled down, but it doesn't hurt to make sure their tight.

Thanks for everyone's help. I talked with the guy at the shop I bought it from and he thinks it's the sensor, or wire on the sensor that tells the machine it's in neutral. I've been riding it almost everyday since i posted this and it runs fine. I start the machine using the electric start by applying the left hand brake. Starts every time. guess i'm going to have to look into the sensor.