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The Roman Painted House needs money; the Western Heights too, including the Drop Redoubt (I'd like to bring the Citadel back into "public ownership" too).
Crabble Corn is run solely by volunteers and needs work doing on it; it also needs publicising to produce many more visitors - the people there work so hard all the time need some financial and moral support.
The Dour needs attention and not just lip-service.
Small businesses need help with their rates (paying them and reducing them), so I would donate £5,000 to each of the small (independant) business.
Smarten up the buildings in Dover - there are so many with good architectural merit, but are now run down and dilapidated.
Fund a Tour Bus in the summer months, so it (them - there might need to be two) can visit all the historic sites and attractions in Dover.
I wouldn't turn the back of the Town Hall into an Hotel, but into luxury flats/apartments, not ones for the homeless, or those on drugs and benefits (yes I know that they need to live somewhere, just not at the back of the Town Hall).
All the approaches into Dover need tidying up - urgently: Folkestone Road (B2011) lower end; A20 along Snargate Street and Townwall Street, especially where the old T.A. building is near the entrance to East Cliff - and along East Cliff too, it is such an eyesore. The side ways coming down Jubliee Way also.
That'll do for starters.
Roger