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The Winch itself needs to be raised so the Strap isn't laying on a edge that could cut it. Perhaps wrapping the Strap the other direction would accomplish the goal
As for the outdrive, I wouldn't run the engine with the drive tilted up fully as it puts the U-joints under...
And the Lower Cowl/Cover is from an 84/85 model.
I used to keep a 71 wrap on my 84 115, just because I hated the Brown, and thought the Red Decals looked much better. Lower cover I left Brown, because I was just lazy, I did have the 71 piece, actually I still have the entire 71 cowl.
If you use a Carb Plate to lift the engine you should be fine, just use bolts long enough to bottom in the intake, using washers under the bolts heads if need be. Also don't subject the Motor to sudden Stops when lowering it.
You say all the Pistons had broken rings? Check the Bore to determine if a previous owner did a poorly done rebuild. If so, I suspect that the Rings were never checked for proper gap, just slapped on and in they went.
Removing the Powerhead will give you complete access to the lower bolts. Someone mentioned adapters, but they can affect the amount of torque that gets to the bolt, and/or the amount of Torque you need to apply
Even switching from 1.5:1 to 1.6:1 rockers will complicate a reprogram
The hardest thing about Carbs and Mechanical Distributors, is making sure the guy buys USCG certified items. Same goes for the FI systems but a lot of Hot Rodders just ignore it cause, they are Special, and rules are for...
I wasn't concerned. I see lots of Trailers without plates. Mine fell off and I towed for a few weeks without it. Made for fewer Photo Radar Tickets
Get a Plate from a friend, or go and resister it as a Homemade Trailer, stamp the Serial with your Name and a #
This is the sequence I've used
What is the Torque Spec?
If it is, say, 18ft lbs, Are you doing 18lbs from the get go, or are you doing 10 lbs, then once all are done, you go over again with 15lb, and then again with 18lbs, and then a 2nd time at 18?