I'm starting to get annoyed with this...
 

Lately everytime I take the bike out it shifts fine, but as soon as I've put about 3 to 4 miles on it the bike doesn't want to shift and you really have to put some force into getting it into the gear you want. I actually have a huge bruise and swollen mark on my foot from it. I'm not crying about the pain, because I'm riding no matter what. I just don't want to screw up my scoot. I'm a complete greenhorn, newb, squid, or whatever you want to call me about bikes but I've worked on cars for years. If this was a car I'd say it's low on tranny fluid or gear lube. Anyone have any ideas? I could really use the help everyone.

Have you changed the primary/tranny fluid?

Without knowing age/mileage of bike...I guess and would suggest that a clutch adjustment might be in order.

It's the bike in my sig. 90 Sportster 883 with aprox 42k on the clock.

And I've not changed a thing on the bike except for plugs and removing the b*tchbar and all the crud off of it.

Yeah,get you a manuel and start getting your hands dirty,she needs a little tlc.

The primary/tranny fluid should be changed every 5K miles and the clutch adjusted at the same time. As said above, you need to get a Service Manual and go to work, especially if you don't know the bike's service history.

Yeah, unfortunately the guy I got the bike from was less than helpful the first time the bike started acting up and all I asked was what has and has not been done to the bike recently. 8 calls and 4 or 5 voicemails later and I've still not heard from the guy. Guess he thought I wasn't going to be cool about it. The bike is a 1990 so it's going to have little things happen here and there. Anyway, back to the subject at hand. I realize I need to get a manual for the bike as I'm finding more and more oil on my cardboard I keep under the bike, and I'm more of a rather fix it myself if I can kind of guy. I'm just not looking forward to chasing down a wiring goblin that has been pestering me. The tach on the bike didn't work when I got it. Well once night it started working then went back out. Also the taillight doesn't light up if I hit my front brakes, only the rear. Granted, you're supposed to use the rear at the same time, but sometimes when I'm just slowing down I'll just use the front brake, but it would be nice to have the retards with cars up my arse know what I'm doing.

Since your handy with cars, I'd say just get a service manual, and do all your own maintenance. These things are "usually" a lot easier than working on a car/truck. For your tach, just trace the wiring back to the plug and check the connections at both ends. The leaking oil, well, that depends on where it's coming from, (oil blow by dripping down from air cleaner, rocker gasket leak, etc), as to how difficult it will be to fix. Oh, and from your sig pic, your bike looks to be an XLC for "custom" model, (chrome cases on the engine, 21" front wheel, forward controls), but that's just a guess based on that picture. ;)

Adjust the clutch on the cable for starters and see if that makes a difference. Troubleshooting 101 here.

You've definitely got a good eye there. I've been told it's an XLH though, but I'm not 100% sure. The forward controls are defnitely something made for some other bike, but they work. lol. The front wheel is defnitely different than the back so I'd tend to guess it was added on. A lot of people don't catch the little details like you did though. My riding buddy didn't notice I had a 21 up front until his dad mentioned it and asked me. I love the bike. The sad part is I've only had her like 2 months and I feel like I've already outgrown it. Once I get back to a stable job and get my Durango paid off I plan on getting a Night Train or possibly a stripped down cruiser. I'll probably still do the 1200 conversion on this bike though because it just doesn't have the power I'm looking for.

So since everyone has advised me to get a manual for the bike, where is the cheapest place to get one? And what manual am I looking for? Remember, new bike guy/old car guy. lol. I know Chilton and Haynes but I have a feeling they won't help me much here. lol.