Joe,
on the hole in the tuning peg, you can consider any of the following:
- take a sharp knife, and trim down a few strands at the end of the string, over ~ 1/2", so that it becomes thinner & you can just fit it into the hole in your metal peg. Do this only if your string is long enough (and don't do it if you don't want to damage your string - these guts are silly prices nowadays). This takes about 30 seconds and does not damage your bass.
- Make the hole bigger. This may leave sharp edges that could damage future strings, and it may weaken the peg. And you may damage your bass in the process. It can however be done very nicely - consider taking the peg out of the peg box. This is a long-term solution for this problem.
- Using a piece of common (mild) steel wire, make a loop around the E-string near the end, and then wrap the ends of the steel wire around each other (using pliers, nice & tight), so that the string is held by the steel wire. Cut it off at a length slightly less than the diameter of the peg, and you're left with a steel extension, perpendicular to the string, which you just push into the peg hole & tune up.