My 2011 RGU 103" has about 35 psi while above 2000 RPM, and about 10-15 psi at idle of 1000 RPM. This is when the oil temp is as hot as I can get it, 100° degree weather and a long ride. Pretty sure the oil pump has a relief valve to limit pressure to 35 psi, because even cold it won't go above that.

I would stick with 20W-50, your motor is probably fine if you get 35 while riding.

 

these numbers seem ballpark for newer oil pump. I think it does run closer to zero at idle than 88s, when really hot

88 when bad traffic would go close to zero too.

There is hot, and then stuck in traffic hot.

Mid 30s riding.

There is pressure relief in cam plate. Though I think it is a lot higher, and mostly heard when cold. Spiring and plunger. Blows open under pressure.

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Clutch adjustment and or a bit to much lube in primary.

 

I don't know guys. I am thinking that if I couldn't move the shifter from 1st to N and a dealer tech told me the fix was a heel shifter, I think I would laugh in his face; that's ridiculous. I don't claim to know what the issue is, maybe to much oil in the primary, maybe poor clutch adjustment, maybe something else but adding a heel shifter is a bandaid and, IMHO, does not address the issue and could lead to a more serious problem if not properly addressed.

OP, if you want to check oil pressure, get your hands on a mechanical gauge and connect it where the oil pressure sending unit is and take readings. Oil pressure on the early Twin Cams could bounce around zero when hot and cause the oil light to flicker but the later models not so much. Check it with a guage.

Pressure relief valve opens at 35psi.

 

HD manual says you can run 60wt if the temps are above 80F.. I can see temps in Florida staying above 80F. You can run 50wt above with temps above 60F.

The specs for oil pressure are a 30-38 at 2000 rpm, oil temp 230.

Personally anything above 0 at 1000 rpm idle is good and IMO anything above 30 at 3000 is good. My 07 EG, has been reading these numbers for the last 50000 miles. 118000 on it now and the motor is built to a strong 107.

As far as finding neutral and shifting goes, if the primary fluid level correct and clutch adjusted properly, it time to rebuild the clutch. The 96 ci motor utilized a 280 lb spring pressure in the clutch. Any miles and they will slips slightly. You won't notice it but it will cause the clutch to wear uneven. Clutch typically needs a new set of plates to restore proper operation.