What advice do you have for a traditional guardsman preparing to retire in the next 24 months?

The absolute most important things are:

Make sure you have copies of all your records from Day one on. Make sure all your medical issues that occurred on IDT, AT, and any active duty are documented. About 9 months before your retirement date, get with a VSO and start your VA claim.

As for your actual retirement stuff, ensure you sign and date every thing correctly so there is no delays in processing. Ensure your point total is correct as well.

Each state runs a couple seminars every year for non-regular (mday) retirement.
Attend one of those as soon as possible, even if it's just on Teams.

You'll want to understand the complete benefits of gray-area (between separation and collecting) and actual retirement.
Your Jordan deployment should qualify for early collection prior to age 60 (6 months for every 6 months deployed after JAN 2008).
And you'll want to get the paperwork right to have that retired pay start on time.

Save everything! Those ‘old’ orders, may be helpful when you file for Social Security!!

The one I don't seen listed is your 20 year letter, or Notice Of Eligibility. That is the official notification that you are due a retirement at age 60. This one is especially important if there is a break in service between your 20 years and the age you can draw.

Ditto on the 20 year letter, it is critical. Verify your points yourself, make sure nothing is missing. I didn't need all my old records, although I have a pile of boxes.
If you're married, don't forget to opt into (I can't recall the name of it) benefits for your spouse if you pass. Yes it takes some money out of your retirement checks, but your spouse earned it! Last I knew you can't opt into it after you retire, or you only have a short time.
I don't know anything about your circumstances, but my recollection is that if you desire you can get Tricare. I retired at 60YO, it was cheaper than anything I'd get through an employer.
When you do retire, enjoy. Seeing a convoy on the way to A.T. has a whole different feeling now!
You'll be glad you stood the test of time to retire. Retirement pay is nothing to sneeze at, and TriCare for Life works well with Medicare. The wife and I have had next to no Copays (except prescriptions).
ENJOY THAT RETIREMENT, I AM!

Get resume ready to go for civilian jobs u want

Anytime its military related:
Document every thing! Nothing and I do mean nothing should be ignored.

Keep names and contact numbers of individuals you served with as you may need a statement from them to justify benefits later on.

Standard reply. Copy of medical records. Make sure everything is in there and make sure the copies are legible.

Copies of all orders and schools attended.

Document,Document,Document.

Save everything! Those ‘old’ orders, may be helpful when you file for Social Security!!

Make sure you have copies of all your paperwork. Especially your points and 20 year letter. Get a copy of your entire medical file. Medical files get lost or damaged. Keep in touch with fellow soldiers. If you file for VA compensation; buddy statements and a copy of your medical file could be the difference between getting nothing and or many valuable benefits. Even if you are not interested in VA benefits now; go to the VA and document any injuries and service. I was told to do that after a deployment and it really helped years later when my injuries had gotten worse.
Then quality of care in the VA varies greatly between locations and Doctors. Some are great. Some others? Do not be afraid to go to other locations. I was told the VA does not do dental implants. I talked to other veterans and I discovered that the VA hospital I first asked did not do implants but another VA hospital 60 miles from my house did do implants. Nobody from the VA volunteered that info. Take advantage of the community care program. If the VA does not offer a medical service near you they will pay for a local doctor. Warning- they are slow to pay
Good luck