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1995 VT1100C2
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So to clarify, you had the fuel valve off, started the engine and then put the bike in gear? This will not hurt anything and will not cause the engine to die unless the carb is out of fuel. But then you could restart the engine so carb was not out of fuel, Sounds to me like engine died due to improper use of throttle or clutch when engaging a gear. Reading your other sympoms I suspect the battery is weak and Swifty has suggested a test.
 

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Can you go over the symptoms again? The way I read the thread you are having 2 issues: 1) hard starting 2) poor performance at low speed. If you can clarify these issues might be better:

1. Hard starting ie you press starter button and nothing or just slow turnover.
What happens with lights etc.
Does it start badly after warmed up ie after your 20 minute ride?
Are you using Full choke; No throttle to start? ( I think that is the procedure throughout the 1995 lineup)

2. Poor performance at low speed.
What happens if you just stand beside the bike in neutral and let it idle then throttle up?
What happens in 2nd gear idle and the throttle up?
 

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...
If I go for a 20 minute ride, come home, shut her down completely and then go to restart - she starts right up...
This is enlightening. To me it sounds like battery is still struggling but may be due to cold plus I would hold the start button for another 2-3 seconds. I would use neutral so you dont need to hold the clutch in. Also try starting while sitting on the bike with stands up (in case there is a switch problem. Start Full choke NO throttle and I think you are doing that. Start buttons are often corroded so if there is no response from the button take it apart.

The "running" video sounds like your pilot jet may be partially plugged or A/F mixture screws not adjusted and a quick fix may not work. I would like you to try this: Start the engine as described but leave the choke full on then try revving to see the effect.

Last question is once the bike is warmed up after 20 minutes it starts well but does the engine run well then ie no problem with revving from idle?
 

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First video is correct for a for a fully open choke. Second video sounds perfect except for a stumble at second :31 but not sure if that was you letting throttle off. Third video sound like bike is starting and running well. I would do the start button as Swifty suggests and pull the spark plugs to examine (even if new) as that is fairly simple and post photo of the plugs. I also suggest do a video of a cold start because the warm start sound perfect.
 

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...Yes, you're correct, the Choke was fully opened there.
This is the cold start video, it was a number of posts up:...
Yes I did see that video however your cranking was about 2 seconds and the engine likely requires 5 seconds for a cold start on a cold day. I would press the start for at least another 2-3 seconds.
 

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The electrode and ground looks good except for the deposit at top of thread. Is that oily or sooty? Based on your other issues I would clean the plugs and reinstall and then check in a few hundred miles. If it is still oily maybe a valve problem and if sooty maybe too rich but for now I think they are great so no problem. With a reasonably well tuned engine I get about 20,000 miles from the original spec spark plugs so I stick with them. Iridium you may get 100,000 miles but I hate to have a spark plug that outlives me.
 

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... But I just keep turning and turning the wrench and the other ones aren't budging. Sometime it squeaks a little. I'm wondering if whoever installed these ones possibly stripped them or if the thread is slightly crooked. The others came out with such ease after only a few turns so I haven't exactly figured out what's going on with these deep ones....
You need a thin walled socket as such in the toolkit otherwise your socket may be sitting on top of the spark plug and just turning.
 

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If you already bought the new ones, may as well use but I would still pop them out in 3-4 hundred miles to examine just because i don't like that oil/soot. I would also suggest using a top tier fuel (PON 87), good oil and stock air filter.
 

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You mention there are service records so if they include a recent oil and filter change then I would not worry, Also that air filter looks good. As mentioned, maybe poor quality fuel was the reason the plugs looked oily as switch to a name brand for a while. The slight hesitation now sounds like gum in carbs so without a full carb cleaning, I would just try Seafoam or Berrymans or just a good fuel like Chevron and see if that clears up the hesitation.
 
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