I'm fairly new to the friction shifting world, so I'm wondering if my bike is shifting correctly.

On my shimano deerhead setup, the shifting process is smooth and the chain seats quickly on the desired gear. But on my suntour cyclone setup, the shifting is a little iffy and very high maitenance. Its not easy to get the chain seat quickly onto the right gear. If I shift directly from the smallest cog to the highest cog, it can cause the chain to rub on the front derailleur. I was running a mixed setup (suntour command shifters) but I am now using the stock downtube shifters and still having these issues. I'm running a fairly unused helicomatic freewheel and sedisport chain. Everything has been completely serviced.

On a side note, I'm having terrible squealing when using my brakes after installing kool stop pads. I tried sanding the pads but the squealing is still there. Does this go away or is there a better pad I should be using?

I know nothing about the Shimano Deerhead, but your description of the Suntour Cyclone behaviour is not atypical for 70s-80s vintage equipment. Part of the required skill back in the day was developing the finesse to shift from one gear to the next, accurately. With practice you whould be able to acquire this skill. There may be some esoteric adjustments that could possibily improve your shifting performance; with some expert assistance and/or trial & error on your own, you make be able to eke out some improvement. It is pretty much a given that the front derailleur will need to be trimmed slightly to accommodate the variation in chain angle from the largest to smallest rear cogs. By this I mean you need to trim it as you ride, in accordance with changes in the rear derailleur position.

I've heard and experienced that Kool Stop Salmon pads are more prone to squealing, and whether it occurs or not seems to be a little be hit-or-miss with each individual installation. You will find that there are a few threads dealing with this if you undertake a search. The immediate steps I would take to investigate this issue are:

• ensure pads are adusted in proper alignment with the rims tangentially, and square to the rims or slightly toed in from a perpendicular perspective with respect to the axle.
• ensure there is no undue free play in the attachment of the brakes to the bicycle, or in the fork assembly to the frame.
• if the bike has not been ridden extensively for a while, it could be a matter of bedding in the rims. Some judicious hard braking, e.g. going downhill should take care of this, if it is indeed the issue.

As a last resort, change to a different type of pads, but, speaking for myself, I can tolerate some squealing in exchange for the improved stopping power of the Salmon pads. Squealing brakes can also serve as an automatic warning for errant pedestrians as well as fellow cyclists.

Depending on the rim, you can also try roughing up the braking surface a bit. Not too rough. Use brown or red Scotchbrite pad. Much easier to do with the tires removed.
Are they aluminum alloy rims?

If the previous pads left black rubber burnished on the rim sidewalls, that could causes squeeling. Scrape or sand it off.

Any anodizing on the rim sidewall can also make for more tendency to squeek.

If the rims are chromed, the salmon pads will always squeek.

Observe the alignment geometry of the pads withe the brake applied lightly and with the bike being forced foreward.
This is the condition where the pad alignment counts.

You will need more toe-in with stickier pads in most cases, since sticky pads tend to be more squeeky.

To reiterate what olds'cool said, on a lot of bikes, the shift from biggest to smallest cog will often require a slight trim of the front derailleur. I have a lot of 80's bike in my stable, and it's not true for all of them, but true for many. But no big, with friction, you have an infinite number of increments to use.

FWIW, the little cogs are intended more for use with the big chainring (both on the outside) and the big cogs are intended mostly for use with the small chainring (both on the inside). It's what mechanics and tinkerers with old gear refer to as minding your "chainline." It's not something I even noticed until I started to mix and match component groups and started assembling 2x7 and 3x7 drivetrains, etc. Heck, I never even noticed the difference in width and length and stepped contours of FDs until I started messing with this mix-and-match stuff, and obviously, it makes a huge difference.

The Deerhead front derailleur probably has a wider cage to handle a triple (touring / mtb group) so there is less chance of chain rub when you run the rear freewheel from bottom to top, the Cyclone front cage is a little narrower and a full pass requires a little derailleur trimming.

You don't do this! Sounds like part of your problem is not understanding how to shift, and I do not intend to offend with that statement. You do not go directly from the small cog to the large cog without shifting the front derailleur in the process.

As for the brake squealing - toe in your brake pads, ensuring that the front of each pad touches the wheel rim first but only just barely. If the front does not touch first, both squeal and shudder are possible results.

Shifting behavior is a good description.
The parts do what you set them up to do, and simply react to your shifting behavior.

1-Anticipate. You should not be going from the smallest cog in the back to the largest cog in the back with one "throw." If this is an uphill after a downhill, position your chain while you go downhill, in order to be ready to climb. That includes trimming the FD.

2-Understand your gears and their limitations. A double FD generally does not cover the entire rear cogset without some adjustment. Also, if you can understand the actual gearing, you may not need to cross all those cogs in back at once, you may be able to move on the front ring and get the gearing you need without large jumps on the rear.

3-There is a learning curve to the shifting. Practice when you have the luxury of experimentation. Adjust your FD/RD and cables, and ride to, not in spite of, your gearing and setup.

Another factor which affects the chainline and resulting front derailleur rub, is the chainstay length. A bicycle equppied with Shimano Deore XT is most likely to have a significantly longer chainstay than a bicycle with SunTour Cyclone. As stays get shorter, the chain crossover angle increases, increasing the probability of front derailleur rub.

With the '70s and '80's bikes with 5x2 or 6x2 that I've owned, the chainline seemed fine for using the small ring with the whole of the rear cluster. You sure could go all the way from the small cog to the large cog or vice versa. Might need to do it carefully to avoid stressing or jamming the chain or even jumping it off the cluster; don't just yank the lever. It was easy to develop a feel for what's ok and what's too fast. Yes, I did have to trim the front a little bit when doing that. The big ring was only good for the smallest two cogs. Big ring with the bigger cogs sounded and felt through the pedals like a crossed chain. So, for me with my only 'average' power, I am on the small ring almost all the time. Big ring is 'overdrive' for favorable conditions - tailwind, slight downgrade.

Some members may call me all wet on this, but here I go:

I do not think that there is a "normal behaviour" in vintage, friction-activated transmissions. They can be eccentric and exhibit different behaviours. And the mix and matching of parts can either enhance or subtract from what you want.

Many people are right fortunate, and they have smooth shifting. Others may have a mixed bag of clitches. I have one bike that runs perfectly on the stand. I have had a professional racing mechanic check it out as perfect. Yet on the road, a cog that should run on the big ring won't run. The selection jumps about from the next bigger cog to the next smaller one depending on the trim. Go figure.

Since I am out for the physical exercise and need some exertion to keep the BP from blowing my brains out, I just live with it. I jump to the small ring and find a similar ratio. It may not be a perfect selection — but I'm out for fun and rec'.

Change up and down the rings, select cogs, then trim. I could arouse the ire of "she who must be obeyed" and buy a modern crotch-rocket in AL/plastic with effortless brifting-shifting, but where would the fun be in that?

Randy's point is right on. And YMMV! But, something suggests to me that you have something out of wack. For one thing, I would check everything that applies to the alignment of your machine — frame, wheel and hub centering, optimum chain-line. A rogue cog is one thing, but a complete pain in the rectum in regards to any selection is not normal.