[QUOTE="Header14]If I put the VIN number in the H-D service site, it says its an 88 and does not list it as a Screamin Eagle but look at the engine photo. Also included engine serial number if that's helpful?[/QUOTE]
The engine case number is a shortened version of the frame VIN. So, if you compare the frame VIN with the engine stamp you should see a sub set of the frame VIN numbers which will verify that the engine case is the same case that was installed in that frame at the factory which is what I expect you will find.
The motor might very well be 103" which would have been the result of installing a Stage I 103" stroker kit, PN 29877-06 which would have been dealer installed. The kit included heads, pistons, SE 253 cams, 4.375" stroker crank and clutch spring. The motor was relatively low compression with published static compression of 9:1. With the late closing SE253 cams, CCP, at sea level, should be about 165psi. You should be able to go to any dealer and enter the VIN and any work done at any dealer on that VIN will show up. If the SE 103" Stoker kit was installed, the cams will be the SE253. If you pull the cam cover, you should be able to see the cam ID stamped on the face of the exposed cam journal.
In any event, your compression numbers, if accurate, do indicate a compression loss which could be the result of many things. Your pictures are not really all that bad. The streaks you see on the cylinder walls are very common and usually occur on break in, particularly if the assembly wasn't as "clean" as it shoud be. There is always some machine grit on rings and if the cylinder walls, rings and pistons were not cleaned properly, the result will be some streaking on first start up which doesn't harm anything. The pictures of the piston tops don't show a lot of carbon accumulation which indicates to me that the motor doesn't have many miles on the last rebuild. The only picture I see that might be troubling is the picture of the valve.
Bottom line? Go back to my previous post, #7 and do the work to narrow down the issue. IMHO, you need to rebuild the top end by boring the cylinder to 3.885", fit a set of .010" OS pistons, have heads cleaned up and maybe a street/Stage I port job done, replace the SE253 cams with an aftermarket cam set to set CCP about 190psi, find a tuner that tunes with the Power Vision, buy a license and have the motor properly tuned. There are some associated upgrades that should be done at the same time, mainly in the cam chest. Keep the cost down by retaining the OEM cam plate, replace the inner and outer cam bearings and replace the OEM chain tensioner pads with a set of CYCO chain tensioner pads. Replace the OEM head breathers with a set of the later stamped head breathers.