The drain plug on the bottom of the travel control valve is an easy to get to low point in the system. If you're inclined, you can run the engine while the drain plug is out of the TCV, but the oil will spray a wide swarth and you need to be prepared for this.
Case/Ingersoll calls for 20W40 engine oil which is not readily available and expensive. Many of us operators use Shell Rotella 15W40 diesel engine oil or a similar 15W40 engine oil. I had put full synthetic 20W50 in both my 1985 448 and 1989 4018 which made cold weather starts easier. I just did some work on my 4018 and put in Shell Rotella 15W40 this time. At $35 for a 2 1/2 gallon jug, it is a reasonable price of $3.50 a quart.
Yes, you could connect an open ended hose into the rear pto and hang the other end in a pail. With the tractor at idle, open the pto valve. It will empty the bulk of the oil very efficiently and as soon as it stops flowing, stop the engine. Then remove the plug on the TCV valve to drain the rest. This or any oil change is best done with the oil hot so as to get the most oil and suspended dirt out. I also prefer to leave it drain overnight, you would be surprised how much more trickles out.
As dundee222 has just said, you can do that, then remove the TCV drain plug and let it drain overnight, so what is the hurry?? Even at idle, 6 quarts of oil will come out of an open PTO hose quickly, be ready for a spray and splash in a few seconds!
(1) I am paranoid about a running engine and a pump running dry. I pull the spark plugs and use the starter to turn the engine and pump. Make sure you put the spark plugs on their wires and ground the plugs, some coils don't like dry firing and can die if not able to discharge.
(2) I have the loop on the PTO, so I take the quick connect off of the loop. I also put a hose on that QC and plug it into the other one. Then the two hoses are clamped in a bucket. When oil stops coming out of one hose switch the valve to empty the other one.
Don't forget to put the rear end in neutral and engage the TCV to flush out the drive motor and lines.
Dry is a relative term. The pump is going to get to a trickle long before it goes "dry". a couple of seconds is not going to be a life or death [for the pump] situation. Just be prepared. Gordy [like usual],has a good point about running the drive motor too.
To me in the first picture, it looks like the end of the Case lift tube that crosses in front of the grill. Sounds like there are issues with the mag cap. I am thinking it does not run, and the strap...