Time to rebuild?

Yahoo!
Those are some very fine numbers.
The trouble you are having would be normal if the plugs are in.Especially if you are tugging on the belt. Well almost normal.
Whenever you shut the engine off, the engine does not stop instantly. The flywheel continues to rotate the engine until one piston starts to build compression. Then the flywheel gets stalled and the beast sleeps.
Now, along you come and attempt to compress the air trapped in that cylinder, and you cannot. There are about 600 cc of air in there, and it wants to act like a big spring. The only thing that prevents that is the friction of the other ring packs.
You almost cannot get enough leverage on the little fan blades. If you position one at a little above parallel to the ground, you might get enough body weight on it to crank it over a bit, if you can manage that without the belt slipping. But as soon as it moves a few degrees, it stops.
When you crank it over backwards, you have to put in enough force to break the ring-pack friction, and you may also be trying to compress some valve springs. So all in all, it is quite difficult. I can do it, but I am 210 and pretty solid.And if I slip, I am band-aiding my knuckles,lol.

But if it is difficult with the plugs ALL out, that is not right.
And listening for LD for a seasoned tech is useful. But for most, I venture to say,less so. The trick is to be able to ascribe a value to what you are hearing and simultaneously feeling on the turn-bar. A very tricky unscientific,if you will,endeavor. Useful yes to someone who has done it hundreds of times, but to Mr. Average, I'm not on board.
But at your pressures, I wouldn't even worry about LD. LD only measures ring-seal at the top of the bore,where it is the most worn, and the rings have popped out of their grooves to their maximum, and so the endgaps are wide open; and it measures the valve's sealing ability. But with a well traveled engine the valve seats look like crap with wide seats and all banged up and pitted, so you never know if a leak is due to a bad valve, or carbon stuck on it, or even rust in cases were an engine has been out of service for a long time. In your case the compression tests pretty good, so I wouldn't be suspecting an LD issue.
If it starts easy, forget about it. Engines with bad LD either start with great difficulty or not at all. Whereas even with 90 or 60 psi compression, it is going to start. I think it would start with every cylinder at 30psi, albeit with some extended crank-time.And it sure won't be excited about it,lol
One thing nobody mentioned lol, is that if this is a manual tranny, it has to be in Neutral.Another is that if the starter bendex is stuck in the ring-gear, it WILL be difficult to turn. But they usually pop out with a bit of rocking of the crank.
I bought a 1.25 Deep socket to reach inside the pulley to turn the crank. Yeah I know it's no fun cranking it from down-under, but the other option is to remove the fan and shroud.
130/140 are really pretty good numbers.
Those short trips are really hard on this old girl. Every choke start is killer. IMO you need a second car, one with EFI, for those short trips. Six miles is what? about 10 minutes from start to finish? The oil hasn't even warmed up yet. The choke could be on for two or three of those. The intake is cold, and you are just getting heat inside, so the thermostat may not even be open yet.No that's not good. That will sludge up your engine real good.
At this time of year,even if you let it run for 10 minutes first, the total running time will still not be long enough to boil all the moisture out of the crankcase.
I think your symptoms are all related to the twice daily short hops.