With your tower height you have solved half of your problem...it's plenty high. Now do yourself a favor get out a bolt cutter, climb to the top of the tower cut off the shakespeare or digital antenna that you have on top as well as the so called premium rg8x white "marine grade" coax and give it to the other guy in town (red and yellow don't mix well...I know)...let him suffer with the poor performance.
#1 You need a professional antenna, one that will last more than a few seasons, and one that is rated in true electronic capabilities...for instance, a professional antenna like a Celwave/phelps "stationmaster" type rated at about 6db gain completely dominates any shakespeare or digital antenna "10db" antenna.
#2 Look on ebay for LD4 type 1/2" hardline heliax If you have a 60' run on the tower, try to find a hunk of cable that will go from the antenna to the radio without needing splice(s). the following is just an example:
Andrew 20ft 1/2" FSJ4 Heliax Coax Cable GR8 4 Ham Radio - eBay (item 290334142314 end time Aug-01-09 06:03:04 PDT)
Hopefully get a role with either N or UHF connectors already on each end, you can always fix any mismatches later with an adapter.
You are going to choke when you find out that the list price for a "stationmaster" is over $1000 or a 4 bay folded dipole like a decible products 6/9db antenna is in the same price range. Keep looking on ebay and craigslist they turn up once in awhile, ask your ham friend who recommended a piece of wire if he knows any hams that are running a 2meter repeater...they may know more about it than the "piece of wire" guy.
If you have to by a new antenna, try to get on to the Tessco radio parts site, they are in suburban Baltimore, they stock the antennas and sell them much less than list price but still in the $600+ area.
Look at it this way: If you yank a 25' grady off the beach tomorrow, you just earned at least $2500 so there you go.
PS a receive pre amplifier is a very bad idea, it will add problems not solve them. If you go with a Celwave or Decible Procucts grade antenna (Just like the CG rescue 21 system) you will find your biggest problem is you can't turn the squelch tight enough to get rid of the radio traffic from far distant areas.