I have a 1988 Sportster. Its a stage 2.5 conversion and I have put 2000 trouble free miles on it in the last few months. It has always had a weird issue regarding starting. When I hit the startbutton depending on where the compression stroke is it will either turn over like a normal bike and start or.. it will just click and after a second it will suddenly start. Its similar to the other high performance high compression bikes I have heard. I took it to the dealer and they installed a new battery and the tech who worked on it told me its normal for a tricked out motor like mine. He has one too and it does the same thing. I have yet to have a problem starting it until this morning. Keep in mind.. I ALWAYS have the battery on a tender. The charging system on my bike works perfectly. I was all checked at the dealer and by me.
This morning..the temp was 36 degrees. My bike is in an unheated detached garage so its pretty cold in there. I haven't ridden the bike for 6 days. When I tried to start it this morning it initially turned over fine but it didn't start. After a few tries it just started clicking. I usually just have to hold the start button in for a second and it will fire up. This morning, it didn't. The starter cable was hot too after holding the start button in several times. I could smell the insulation on it cooking a little. My headlight is super bright btw.
I was thinking that I should replace my stock starter with one of the 1.4K or higher starters. Some guys told me that it won't help, others said it will. Is this normal for an old Sportster to have issues when its cold. I am looking forward to riding right up until it snows but if I can't get the bike started I guess I won't be doing much riding anymore.
Any suggestions are greatly appreciated.

 

A high torque starter is nice on a motor that has ben modded, but have you checked the cables? From what you said,"the starter cable was hot", sounds like a losecable to me.

 

Ditto, check the cable connections and don't forget the negative ground to the frame.

 

All the cables on the bike are brand new. I checked all the connections and they are all mint and tight.

 

Check the battery, make sure it has a good charge, I know you said you have a "tender" on it, just need to eliminate things. Next, check to see if you are getting a spark, pull a plug and lay it on the head with the plug wire on it and hit the starter.I know this sounds stupid, but, is the gas on? Don't even ask how I thought of that question.

 

Put your volt meter across the cables and try cranking it. That is, put one lead on one end of the cable and one lead on the other end of the cable and have the meter set on the volts scale. 20V range would be a good starting point, but you may need to go to a lower range depending on the meter. If you see a significant voltage across the cable when you crank it, then your cable is defective, regardless of it it is new or not. Other possibile issues you could be having are the starter solenoid (do the same test across it), too much compression for your starter motor to handle, weak starter motor or oil too thick. Are you running a full synthetic? Might help out with your cold starting.

Our '87 883 has no issues starting in the cold.

 

If your cable is getting hot, the ohms have taken over. The resistanceis most likely tobe caused by loose, dirty or corroded cable ends. I know you say they are new cables but I would still double check to make sure that ALL 4 points of contact are clean (physically and chemically). Twice a year I dismantle my cables now, clean the ends with a wire brush and sandpaper, do the same on all 4 points where they connect, and then apply dilectric grease to all four connection points and the cable ends. This lack of good contact problem caught me off guard once, but will not do it a second time!

 

I am running Mobil 1 V-Twin Full Synthetic. The motor is a 1200 done by Johnson Engine Technology. It is a 10.5-1 compression motor so even at optimal conditions it doesn't turn over like a stock bike.
I spoke to Bob Johnson though and he told me that I didn't need a high torque starter. It has the stock 1988 starter for an 883 (the bike started its life in 1988 as an 883 Hugger). It is now a 88+hp 1200 that had $5000.00 worth of work (between parts and labor)done to the motor alone.
When you are talking about the cable.. do you mean the cable that goes from the positive terminal on the battery to the starter?

 

It got hot enough this morning (and one other time back when I first got the bike) that it actually had a little puff of smoke come from the starter cable. Like I said... all the cables are brand new with gold ends on them. I had them all checked out by Harley and they told me they were all mint. I will check it out again. Maybe they missed something. I don't know if this is related or not.. but... I recently replaced my handlebars with mini apes and I replaced my turn signal lenses and bulbs with smoke lenses and amber bulbs. Since I did that only my right blinker works and its pretty slow. My left blinker just lights up the bulbs but it doesn't blink. That sounds like a ground issue too.

 

Definantly check the ground cable, and maybe somewhere your wires touched over heated and shorted each other out on the turn signals. Its weird, but things happen.