On to problem number 2 - since you have the entire 3.5mm connector, the IPhone will think you have headphones plugged in and nothing will play out of the speaker. That's totally unacceptable. If you cut off the tip, there won't be anything to touch the contacts inside the IPhone headphone jack.
I used a jeweler's saw to cut off the tip at the first black plastic insulating ring.
Jeweler's saws might not be all that common but there are other options. A hacksaw might work, a dremel cutoff disc, etc. You might even be able to use the side cutters again but I didn't want to risk bending the part I needed so I decided sawing was preferable to snipping.
I filed down the cut area to remove and burrs and smooth it out overall. I made sure to wipe it down really well so that no filings would end up in my phone.