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Onto the shroud? surely you mean onto the forestay?

Not recommended if you have a genoa furler as it can kink the foil if the spinnaker fills with a bang.

Every sailmaker's instructions for flying one loose with just a tack line say to get the tack line turning block on a strong point as far forward as possible.

I'd look at getting an eye big enough to attach a block with a swivel snap shackle welded to the top edge of the bow roller  port side plate.

The deck light is only used for short periods.  It doesn't really matter if that section is LED or not as the power savings on 5 minutes or less of usage per hour are negligable.  Its usually a 10 or 20W 12V halogen spot light bulb with a bi-pin base available off the shelf in any good hardware store. 

An all round white at the masthead is difficult to pick out against shore lights and may not be seen in time by fast small craft overtaking from astern.  They are looking at the water where they are going, not up in the air.  I certainly wouldn't eliminate the dedicated steaming light, though I do have the bow light + masthead all round white wired on the selector switch for backup use or if I'm motor-sailing sufficiently far out for shore lights not to be an issue.   I also don't use the tricolour if sailing inshore for the same reason.

I assume you mean a combined masthead tricolour and anchor light  and also a combined steaming and deck light on the front of the mast at approximately spreader height.   Both can be wired with three core cable, sharing a common negative return for the two functions in each unit. In the case of the masthead light, you never have tricolor and anchor on at the same time so the voltage drop in the common return wire is no greater than for a single light.   For the steaming and deck light, the only time both get used together is when the engine is running and the higher charging voltage is enough to compensate for the extra voltage drop due to sharing a common wire.

I replaced both without removing the mast base.   The old wires unfortunately had been secured with globs of expanding foam so they came out in pieces with considerable effort and the chunks of loose degraded foam were a real PITA to  break up and remove through the tiny access holes I had.   Replacement wasn't too tricky as I have a permanent mousing line through the mast from head to foot so I could use it to fish into place two lines, one to pull each cable through to its correct hole.   I put pairs of cable ties with the tails left long at approximately 3' intervals as I pulled in each cable to stop them slapping around too much.

However your mast cabling may be fixed in a totally different way - some makes of mast sections have an internal track for special conduit or to take slides fastened to a cable bundle at intervals so before doing anything you will need to figure out how the existing wiring is secured.

Depending on the amount of wear on the rivet holes you may need to go up a size and they will need to be Monel or stainless which require a significantly higher capacity rivet gun to set than aluminium ones do.  Also if the mast base is not already loose it may be very difficult to remove without damage.   Talk to a real rigger before doing anything too drastic . . . .

It depends what you are hoping to achieve.   You will be lucky to get more than a couple of knots in smooth water and an offset small outboard + a long keel is fairly marginal for manouvering in marinas unless you have a crew member squatting on the stern deck manning the outboard controls and steering it.   You will need to remove it and stow it inboard in heavy weather or it will get drowned.    You then have all the issues with stowing petrol aboard.     

How 'removed' was the old inboard?  If the shaft and sterngear are still there consider reinstalling an inboard.  If on the other hand, everything has been ripped out and the shaft log etc. glassed up, it is a far bigger job.   Do look at costings closely.

I belive you are planning to go off blue water cruising?

The other issue I would be concerned about is the vulnerability of your new stemhead fitting to impact damage and the single point of failure it represents.  It's obviously built like the proverbial brick outhouse, but if you ever prang that bow roller badly, you will be worrying about the rig coming down and will have great difficulty jury rigging a secure forestay attachment or even getting the fitting repaired in smaller/more remote ports.   

Consider going back to Stainless Outfitters and getting a carefully fitted strap down the stem added so the forward edge of the fitting can be effectively through bolted.  You cannot afford to rely on undersized fixings that far aft with the amount of leverage the bow roller has. Without the stem strap, I'd want at least 7/16 bolts with some of them out near the corners.  As-is, I'd be worried about the potential snatch loads on the roller riding out a bad storm in an anchorage.

You might want to get a suitable attachment point for an assymetric added at the sme time, even if you currently aren't planning on carrying such a sail.

Whatever you use, it mustn't promote crevice corrosion.  As the wire isn't oil free, you are *NEVER* going to get perfect adhesion from any setting caulk and that's asking for trouble.   My first inclination would be to go with a 50/50 mix of Lanacote and Duralac, but lets see what the experts say

There's something wrong there.  A #4 headsail is a heavy weather sail smaller than a working jib but bigger than a storm jib.

The numbering goes in the opposite direction to the sail area. #1 is the largest genoa you can carry and #5 is a storm jib.

Perhaps if you posted the actual sail dimensions we'd know what you were offering.

Got an edge on view of the sheave?  It *may* just be possible to clean out the wire groove then build it up with epoxy and Kevlar roving to an acceptable profile.   

Otherwise any competent machine shop could duplicate the sheave in Tufnol with a press-fit Oilite bronze bushing.   Unless the pin is in excellent condition, it needs replacing at the same time as if it is worn the new bushing will rapidly degrade due to uneven loading.

Be aware the pin may not be true in the sheave box and this can result in a new or rebushed sheave jamming under load or even the need to increase clearances excessively to get the sheave to turn freely. You may need thin washers cut from UHMWPE sheet (preferably molybdenum disulphide impregnated UHMWPE) to take the side loading and prevent jamming.

Possible as-is if moored in still water directly between two boats with the same height or higher masts with strong enough spinny halyards + a competent team under the direction of someone with an appropriate background in high load handling by traditional ropework.

Personally, I wouldn't care to tackle the job that way as I don't have enough high load overhead handling experience to cope with the unexpected elegantly.  Get it wrong and you put the team and the other boats.at risk. 

Otherwise you need a pivot at the mast footwith a safe working load at least 5 times the mast weight  (or preferably a tabernacle) and a substantial A frame.   It is possible to use the boom as a gin pole, but the bridles for lateral support must be substantial, very low stretch and taken to high load pivot points that are dead in line with the axis of the mast foot pivot.

By the time you've got the gear to do it, unless you are going to use it often, craning is probably cheaper.   And Yes, I have sailed a yacht with the A frame setup and used it to drop and raise the mast for fixed bridges while underway.

Two Rolling hitches or a Prusik loop done with flexible cord approx 1/3 the stay diameter will hold reliably on 1x19 wire.   Pop the toggle at the top corner through the loop and push it up the stay to the desired height.  A half hitch round the stay just below the flag holds it close to the stay, and if the tail is thin enough, two rolling hitches will hold the flag taut, otherwise use another Prusik to tie off to.

N.B.   Take the Prusiks off the stay when you take the flag down when you leave the boat - you don't want a buildup of dirt excluding oxygen from the stainless surface as that can cause crevice corrosion.   

P.S. If you clamp anything round a stay use Duralac to reduce the risk of  corrosion.