Old LOR validity

[upontherocks]

2020 MD grad, currently a GMO (general merical officer doing outpatient care in the US military) applying for residency. Question is would a letter of recommendation from an attending during my clerkships from 2019 I excelled on be worth having when I apply. I've been in touch with people from my school who want to help any way they can so they know what I've been up to and the attending would use my PS and CV to update the letter (something like when Dr X was a student he did this and that, and has continued to show he would be a good resident for Y field as X has these achievements as a GMO).
I made a previous thread with my background details but in short USMD steps 23x/24x/21x, no research, no obvious red flags except being a 2020 grad and FM clerkship I had to remediate with a 2 week elective but under the impression from the clerkship director it shows on MSPE I passed (I haven't seen it but imagine whoever reviews my package I'm sure could read between the lines and know what happened there).

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[NotAProgDirector]

Your prior thread is here: Applying to residency years after graduation (For others if they want to review).

I agree with everything in the prior thread:
1. Your military service will be seen as a positive, not a negative.
2. The "must have graduated within X years" doesn't apply to your situation.
3. You're likely to do just fine in the match for IM or FM
4. You can absolutely get an Occ Med spot if you're interested. Your TY would count as your PGY-1, so you could start as a PGY-2. Occ Med is not competitive.
5. Funding is unlikely to be a big issue. And whether training is funded by the Military or CMS doesn't matter -- it all counts.

Regarding your actual question, it's fine to get a letter from medical school. If you're applying to IM, you're going to want a "department" letter (also called a chair's letter). You'll contact your medical school to see if they will generate this for you. They may be unable to do so -- and if so, don't sweat it. So your letters should be: 1) Your CO / Supervisor about your current performance, 2) A DoM Dept letter if possible, 3) One letter from a preceptor in medical school if they are willing to do so. The 4th letter should be from someone with whom you are working now. When applying to FM or Occ Med positions, skip the DoM letter and include another current letter. If you're interested in Occ Med, I'd see if you can find someone to work with now, to generate an Occ Med specific letter.