I had a lot of personal stuff going on and I dropped the ball. So - on the SP-248 form, would this now be a resident permit or renewal?

Question 8, line M - Do you currently have a valid permit - do I say yes and put down the expired date?

I've heard that the documentation for #9 isn't required if you have had a permit in the past. I do still have my original documentation
from the class I took many moons ago, but I don't know if I need to attach a copy or not.

Edit - I'm in Henrico County.

Any and all help would be appreciated. I really want to get the process started, since it will probably take some time for my new permit
to get issued.

Thanks!

If your previous record can be proven, then push for renewal.  The level for their review is largely dependant their existing record.   No doubt there are localities that will make you start all over, but most would consider the former.

It should be a renewal and a copy of your prior permit is adequate proof of competency, even if it is expired.  There is nothing in the related section of VA code that defines a maximum amount of time that a permit can be expired before it is no longer considered a renewal.  

For Question 8M, check "yes" and list the issuing circuit court and the expiration date.

^^^ This.

I was in the same situation 2 renewals ago.

Old permit should be fine.  Suggest that you call the clerk of the court to doublecheck.  Maybe they can provide clarity on what they need.

Mine expired and I just put that I had a valid permit. Had no questions, got my new permit in a week or two.

A lot of this depends on local politics.
As in the County or City government.

If the CA (Commonwealths Attorney) is a Dumb they often drag their feet.
Like taking the whole 45 days they are allowed.