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Do a search for "Catalina Smile."  That may be what you have going on with the keel.  There will be some good general guidance in those search results on fiberglass repair.  You'll have to explain more about the bilge and mast opening issues - can't really tell anything from the photos. 

FYI, CY's written instructions for replacing the windows is in the Tech Wiki.

http://c34.org/wiki/index.php?title=Instructions_for_replacing_large_fixed_side_windows

Because you have to take the top of the mast assembly off and that is how the forestay and backstay are attached to the mast.  I remember seeing photos on this site of how someone managed to do it with the mast up but it struck me as a lot of work with a fair amount of risk for not much benefit.  Do a search and I am sure you will find it.  IMHO, think taking the mast down every few years is a good safety exercise to inspect all of the rigging and fittings for corrosion plus you can do things like replace the sheaves and lights, etc.   

Garhauer is a good source for the replacement sheaves that are aluminum running on ball bearings instead of the cracked plastic originals.  Mark Felgenhauer will know the right sheaves for your C34. 

Sorry, to clarify, the first bleed valve on the M25XP is on the fuel filter that screws onto the engine (starboard side), not the Racor. There are detailed instructions for bleeding air out of the fuel lines in the M25XP in the Tech Wiki, I believe.

Did you bleed the air from the top of the spin-on fuel filter? With the M25XP, you need to bleed air from two spots.

As to the Racor, are you sure the filter is seated properly? And did you change the gasket when you replaced the filter?

I would expect that these transducers are connected to depth and speed instruments.  Wouldn't it make sense to feed the depth and speed data from the instruments to the chartplotter using NMEA 0183 rather than trying to wire the transducers directly to the chartplotter through a converter?  That is a more conventional approach. 

Here is the link to the Raymarine ITC-5 for converting analog transducer signals to SeaTalk Ng, which is the Raymarine brand on their NMEA 2000 system.  Note that the ITC-5 data has to run to a Raymarine i70 instrument in order to calibrate the transducer data.  It would then be fed into the Sea Talk Ng system.  However, if you do not have an i70 instrument, the ITC-5 will not work - the transducer data needs to be run directly into the instruments.  That is how our system is wired - analog transducer data runs to the instruments and then the data is run throughout the system on SeaTalk Ng (including to a Raymarine E90W chartplotter and an i70 in the salon). 

http://www.raymarine.com/view/?id=3338

Perhaps there is a way to do this with Garmin or B&G - I do know that Raymarine equipment does not work and play well with other systems. 

This might be a good time to check the water level in your batteries if they are flooded.  You can also probably check "equalization" off on your list of things to do for the next six months.   

Have you looked into the Lewmar folding wheel? 

Certainly no disrespect intended to the Mark II boat's sailing abilities.  Roc is certainly right that too much heel is generally an operator issue.  To Stu's point, though - shorter sailors necessarily includes kids.  We raised our twin girls on our Mark I boat and it was good that they were always able to brace themselves easily.  We now own a C387, which if you measure by the cost of cockpit seats, has the largest cockpit ever made by Catalina, so sliding around is definitely an issue with us if we start to heel too much.  But we have the centerline cockpit table, which I actually like and do not find to be a hindrance while sailing. 

I thought of another difference related to weather helm.  The Mark II boat has the larger, elliptical-shaped rudder that is going to help the boat stay on track and fight off the weather helm that shows up when the apparent wind gets into the teens.  Again, to Roc's point, better to avoid weather helm entirely by reducing sail so you don't need the bigger rudder surface area to keep the boat from spinning up into the wind. 

I agree that this comes down to personal preference and whether the perceived advantages of the Mark II boat justify the additional cost.  Here are some considerations I can think of based on owning a Mark I boat and spending a lot of time on a friend's Mark II boat:

1.  The Mark II cockpit is wider and therefore better for entertaining/relaxing while the boat is stationary.  The Mark I cockpit is better for sailing with significant heel. 

2.  The interior of the Mark I boat usually is oiled teak and darker than the varnished and sealed teak on the Mark II boat.  The Mark II boat also has overhead lights and the porthole window between the two storage cabinets in the salon.  To me, this is the biggest difference between the look and feel of the two boats. 

3.  The Mark I boat has a lot of exterior teak and the Mark II has little or none.  You may like the look of the exterior teak but it involves maintenance or it is going to look terrible. 

4.  I think the Mark I boat has more out-of-sight storage in the salon with the cabinets that have the plastic sliding doors.  On the downside, you have the black plastic sliding doors.  We replaced ours with teak plywood.  The Mark II boat added a cabinet in the aft cabin. 

5.  I don't know if the 1986 is deck-stepped or keel-stepped - it could be either, I believe.  A keel-stepped boat is going to have water in the bilge any time it rains.  The Mark II boat is deck-stepped so water in the bilge will be less of an issue.   

6.  A small thing but I hated the head sink on the Mark I boat.  It is right under the cockpit floor so it was a pain to use.  Catalina adjusted the orientation in the Mark II boats so that it was not directly under the cockpit floor.  Another small thing on our Mark I boat - no overflow tank for the engine coolant - just a hose that dripped coolant in the engine bilge every time the engine ran. We added an overflow tank. 

7.  Check out the important upgrades page.  You'll need to address several of those issues on the 1986 boat if they have not been done already - engine wiring harness and alternator bracket in particular. 

8.  I don't know why but engine and filter access was worse on my friend's Mark II boat than our Mark I boat.  He did not have a side panel in the aft cabin to access the dipstick.  His Racor filter also was under the mattresses in the aft cabin - ours was under the sink in the head.  He did have a hinged lid in the aft cabin for access to the back of the engine, which was good for access to the transmission fluid dipstick. 

I guess in terms of my overall opinion, I preferred sailing my boat but I liked living on my friend's Mark II boat better.  Just more proof that every boat is a compromise so the challenge is finding out what matters most to you and your significant other and determining how much you're willing to pay for it. 

If you do a quick search on Flexofold, you will see many C34 owners with M25XP engines reporting happiness with the 15x10 three-blade prop.  You'd probably be fine with a 15x9, as Flexofold tends to recommend, but you probably would not get as much forward speed, particularly in chop. 

I recommend that you purchase the prop through a dealer here in the U.S. instead of from Flexofold directly so as to avoid customs charges.  That was an unwelcome surprise (almost $90) when I purchased my second Flexofold. 

Ron, what did you see in the photos that pegs the boat as a 1988? 

Not exactly on point but what is going on with the alternator?  Is that corrosion on the top?  There was the starting issue that was bypassed by delivering a charge directly to the starter.  I wonder whether the alternator was involved?  If I remember correctly, the wire from the A/B switch runs to the alternator first and then there is a jump wire to the starter. 

This is a very good article on feathering and folding propellers.  This debunks a lot of common "wisdom" about both. 

http://www.yachtingmonthly.com/gear/folding-and-feathering-propeller-test-29807

Keep the old rudder post because you will need it to size the new rudder post and to have the holes cut into the new rudder post for the quadrant and the top bolt to hold the new rudder post in place.  Catalina sends the new rudder with an oversized post and without holes so that it can be customized to your boat.  The new rudder post is double-walled stainless steel so you may well want a metal shop to do that work.  I would order that rudder sooner rather than later because it is going to take Catalina a while to get it made.  My memory is that ours took about six weeks to ship, which was two weeks longer than they originally predicted. 

All good advice in terms of sails.  A couple of other considerations:

1.  Our C34 had a lot of weather helm.  We originally had to furl in part of the 150 headsail when the wind got above 12 knots apparent.  Moving to the new rudder helped keep the boat from spinning up but the best change we made was to move from a 150 to a 135.  That helped move the center of effort forward and put the boat in better balance.  Part of that also was that a new sail moved the draft farther forward.  We could then keep full canvas up into the 15-17 knot range.  You don't see a lot of sailmakers recommending a 150 as an all-purpose headsail anymore. 

2.  If you are looking at getting a new main, you might consider adding a Strong track system to make it easier to raise and douse the sail.  We've had the Strong system on two boats now and think it is really worth the money. 

3.  Again with the main, you might also think about what sort of sail containment system you want.  Some people really like the "sail pack" system because of ease of use.  I personally don't like lazyjacks and think a well-installed Dutchman system works great.  You'll get as many opinions on that as you would on religion, politics, and propellers.  This is a good time to try to figure out what works for you. 

I believe that is correct.