Yo-Yo Weight and Loose Skin

Hi there, this might be my first post here, despite being a member since 2012 ✌  So this might be a bit long.

To begin, I've browsed several threads here: questions, success stories, articles, etc., on the topic of loose/saggy skin.  I'm aware that factors will vary, such as genetics, age, weight history, skin condition, exercise regimen, diet, etc.  So I know results will vary.

I guess I'm looking for someone who's been in a similar boat as me, so I know what I could realistically expect.  I'm 37, female, 5'7, currently 183.  My weight history is very up and down, and roughly looks like this:  was always a larger girl, was mildly chubby as a kid.  In my mid-teens I was on the road to anorexia, got to about 150, not bone-skinny, but definitely not healthy.  Turned that around and went up to 170-175, right before I got pregnant at 20.  I kept getting told I "carried it well" (AKA didn't bloat up) and put on about 40 lb.  Dropped back down after my son's birth (not sure of #) but started gaining about 2 years in due to my own negligence.  Started going to the gym, got down to ~198 at about 24 yrs old, but then "a lot of life stuff happened" and ballooned up to my highest of around 280 when I was around 27-28. Turned that around, and reached 240 before joining MFP in 2012.  Been on and off since then, but at least in an overall downtrend.  The last 2 years I've been mostly good.  (If it matters, I'm currently at around 1500 cal/day.  I'm still fixing my relationship with food, but I think I'm the best I've been in years. Doing some bodyweight, HIIT, and playing RingFit mostly every day, and considering adding lifting, since I have some weights at home. Anyway.)

I'm currently 183, the lowest I've been since I've had my son (who's 16 now, holy cow!), very close to my prebaby weight of 175, then I'm going to reassess where I want to go.  I do have some sagging on my lower tummy and signs of it on my arms, which to be fair, is not as bad as it used to be, but its still there.  I know there is still fat to lose, but with the length of time I've had this weight, the up-and-down history, and the addition of pregnancy stretch marks (which don't bother me), it adds more factors.

So all that out of the way... anyone have a similar situation?  If your skin shrunk back, how long did it take, and what actions worked for you?  I know my story sounds overly specific, but I can't imagine I'm the only one with this kind of history.

I understand skin shrinkage/healing is going to come with time, the question is how long.  I'm not against the idea of surgery, but I'd prefer that as a last resort.

TL;DR, up and down weight and a pregnancy over a 16 year period, is my skin going to recover?