When should I expect my first pay check from VA and TDLR?

Going thru the whole VA process can take quite some time. After I got it took a year and a half before I got my 1st check. I did get a lump sum that back dated. It also depends on what state you go through. I was in California because that was where my then boyfriend was stationed. I was also wrongly told I could only put down 1 disability. I wish you luck with your process. Seeking advice from the local VA office can really help.

Disability payment benefits for a particular month are paid the first business day of the following month.
If the claim has been decided before you separate, you should expect the first payment the first day of the month after you separate.
For example, if your claim has been decided, and you separate on 4 May, you would receive your payment for 5-30 May on 1 June.

A service member is placed on TDRL only if his condition is not stable, he has Total Combined Military Disability Rating of 30% or higher, and there is a chance that he could improve enough to return to full duty or seriously worsen within the next five years.