I'm not sure what you mean by standard cable connectors where you splice the cable. To me, standard cable connectors are VHF connectors screwed together. That's fine, but each one will add about 0.2dB of loss if done properly. You aren't limited to just pl259's which are very difficult to solder properly. N connectors are easier to put together, generally less lossy, but more expensive.
The dielectric grease is useful on threaded connectors, but not necessary if properly sealed. I wouldn't get it anywhere near the braid or center conductor of the coax cable though for the same reasons mentioned by MS.
The cable loss is something to keep in mind, but your choices ( cost) are pretty good at VHF. I like LMR240 cable. It's about the same size as RG8X, but has much better loss figures and is reasonably priced. At VHF frequencies, the loss with LMR240 is 3dB per 100'. RG8X-5dB, & RG58u is over 6dB. RG8x and RG58u are typical of the types found at Radio Shack. A good rule of thumb with regard to this term for loss is for every 3dB of loss, you effectively cut your power in half. 25w transmit power is now 12.5 at the antenna, 6dB loss would be 6.25, 9dB=3.125w and so on. Actual noticeable performance differences aren't as bad as that appears though. Typically, a receiver will require the transmitting station to increase it's power 3dB ( double) to notice a difference. That includes a station transmitting at 10 watts or 1000 watts. Every little bit does help and is compounded with cable losses and antenna gain.
Your antenna is probably rated for some degree of gain as well. This doesn't mean it amplifies your signal, but it redirects energy from useless directions, like straight up or down to horizontal. Picture a spherical ball and then a flat disk. The higher the gain, the flatter the disk. Some antennas focus the radiation into a single direction and extend their range even more in that direction.
If you have 3dB of loss in your cable, and 3 dB gain in your antenna, you end up with effecticvely the same signal as you would with no cable loss into an antenna with no gain. The gain vs loss does cancel out, but noise is increased and that reduces receiver performance. All in all, it isn't a big deal unless your cable runs are over 100'.
My point in this is to try to explain how it works and to let you know that the losses you are likely to incur on a 25' boat are not horrible, even with the cheap cabling. Installing connectors properly and good weatherproofing will be what makes it work best and last.