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Every once in a while I run a water hose in the forward drain to help clean it. It does accumulate a lot of dirt, but I much prefer it over the 1973 I ran that did not have the forward drain.

Other than sitting out side and being neglected, your hull doesn't look that bad. Coincidentally, my boat had the same damage to the port quarter as yours - it had been repaired (somewhat poorly), and someday will get a proper repair but I am in no rush. If your only major damage is the port quarter and that small hole on the starboard side, don't remove the cap for repairs. Neither of those holes are in a critical structural area, both areas are fiberglass only with no wood, and both are accessible from the back side.

I replaced my in-deck fuel tank in 2011 as it was leaking badly. Florida Marine Tanks in located somewhere in North Carolina, so you may get lucky and not have to incur much shipping cost. With my Honda 150, 40 gallons gives me a 200 mile range, which is plenty for me. If you do require more fuel, there were optional saddle tanks that went under each gunwale that added (I believe) another 40 gallons. There was a gentlemen on the other Whaler site that had a set for sale about a month ago (Michigan, I believe). If I ever needed additional fuel, I would add the Montauk on-deck fuel tank under the RPS that you already have to increase my fuel capacity.

The fabric liner on the inside of the cap? You really have no choice but to tear it out. The previous owner painted the inside of the cap white on mine, and I like it.

I lived north of you in Greenville about 15 years ago. I like Wisconsin so much better for many reasons (including the fantastic beer).