I'm not very familiar with the 260, but my 23.5 has an area where the outboard mounts that would allow a hole to be cut into the side. Inside on the 23.5, this area has no liner is fairly easy to access. I would try to find a similar place to pass the cable through that is not of the top, but rather the side to help prevent water from penetrating. A drip loop before it enters will stop any water that wants to run down the cable. Don't buy into anyone telling you that you have to use large diameter coax like RG213 or LMR400. Your run will be short and the RG8X or RG58 that may come with your antenna will be fine.
The hardest thing for most people, and many don't realize, is properly installing a PL259 connector. There are lots of methods people use to get them soldered on properly, and I'd suggest you search Youtube for some instructions. I like crimp-on connectors myself, but that requires a specific crimping tool. Don't crimp a connector with pliers, unless your making emergency repairs and that's all you've got. I also reinforce the connector with 3 concentric layers of heatshrink at the base of the connector. Where the cable attaches to the connector is a major stress point and I have never had a cable with three layers of heatshrink fail at the connector. I have test cables that I've used regularly for over ten years that are still in very good condition because of this.
If your antenna has a connector at the base, seal the connector with electrical tape at the least. It will last a few months in the weather. Tape is fine, especially if you trailer and disconnect it often. If it were at the top of the mast, I would seal with butyl tape. First, a wrap of electrical tape to make removal of the butyl easy if necessary, then a wrap of butyl tape over that, then wrap the butyl in electrical tape. This is how professionals seal connectors on exposed connectors and I have seen some after ten years or more still sealed.
Don't know which antenna you are installing, but height is the single most effective thing you can do to improve performance.