I experienced many issues similar to the ones you have described that ended up stemming from the soldering iron I happened to be using at the time. I was using a Weller SP40NKUS which is a 40w iron and does not have any kind of temperature control. I was constantly burning PCBs, lifting pads and going through tips like you would not believe. Come to find out, the iron was running at about 480c (eek!). Shortly thereafter, I switched to a Weller WES51 which has a proper temperature control circuit and have not had any issues with tips degrading or burned PCBs and I get perfect joints almost every time.
It doesn't take much heat to melt solder, however, the heat has to be able to transfer into the solder to do what it's supposed to. If there is a layer of oxidation insulating either the pad or your iron's tip, heat will not be transferred. It seems you were experiencing this problem as you said your tips were oxidizing quickly (possibly from the iron being too hot or just low quality tips). In response, you increased the heat of your iron which likely only exacerbated the problem, causing the tip to oxidize further while still not conducting heat properly.
You could try using some better quality tips or a different iron which has better temperature control. Try to keep the heat a little lower to avoid corroding the tips as quickly and prevent damage to the PCB. I usually keep my iron set around 350c for this kind of work. Simultaneously heat the pad and pin directly with the tip and flow the solder onto the pad, not the iron. The solder should melt almost instantly. If it does not, remove the iron and investigate what is preventing the heat from transferring properly. Try using some flux on the pad and keep your iron's tip tinned. Clean the tip with one of those brass wool tip cleaners and re-tin the tip. You shouldn't have to leave the tip on the pad for more than a couple of seconds maximum. Using a good rosin-core solder helps as well.
As far as the chattering, there were some issues with the Zealio switches (also manufactured by Gateron) chattering after being soldered if too much heat was applied as the bottom of the casing would melt a little bit around the pins, altering the shape of the leaf inside the switch. I don't have any standard Gateron switches lying around to test so I'm not sure if they also have this issue. Obviously if the original switch was chattering right out of the box this probably isn't its problem but it might explain the replacement switch chattering as well.
More
Note the melting around the pins of the switch on the right.
Good luck with your board!