HI Concord, Welcome to the forums!
First things first - congratulations on your sober living. Overcoming such a battle is commendable.
Second - congratulations on your decision to repair past credit mistakes. You already have some funds available to begin the process so you're in better shape than you might think.
With regards to that credit fixing:
1) Ignore Credit Karma scores. You need to obtain and monitor your FICO scores for all three burueas. FICO scores are what the overwhelming majority of lenders use to determine credit worthiness. Learning where you stand in FICO land is required for successful rebuild. Credit Karma scores are based on the Vantage 3 scoring model which is a completely different, and quite useless, animal that does not respond to changes on your credit report the same way as FICO. The only thing Credit Karma is good for is montoring your actual reports so you may stay abreast of any changes.
To get started, you can view all 3 FICO scores at Credit Check Total (https://www.creditchecktotal.com/) - sign up for the $1, 7-day trial. Be sure to cancel the trial if you are not willing to pay the monthly fee for monthly scores & reports. I highly recommend you invest in a monthly FICO monitoring service. You can opt for Credit Check Total, myFICO, or Experian Credit Works -- those are a few of the best known sources (myFico is the more expensive of the 3 but it also provides scores from like 27(?) different FICO models). Right now, the most important score for you is FICO 8.
2) Can you provide the Date of First Delinquency (DOFD) for each of the debts you've listed? This will help determine what your best steps forward would be. The DOFD is the date (month / year) the debt first became delinquent and was never brought current, leading to its charge-off status. I'm assuming the DOFD was pretty recent - like 2016-2017-ish, based of the 2024 removal date noted on your Transunion report. (FYI: Transunion generally removes 6 months early (6months before the 7 year mark). Experain is 3 months early. Equifax is 1 month early but you have to request it.)
3) Find out what the Statute of Limitations (SOL) is for your state. If any of your collections are out of SOL, you have more leverage with negotiating a settlement as the collection agency can no longer pursue the debt through legal recourse (they can't sue you). If your debts are still within SOL, you want to take care of them right away to prevent being sued.
4) Are your reports showing both the charge-off from the original creditor and a collection tradeline from the collection agency for all debts?
I ask because although you may have success with removing the collection accounts, you will likely see no success in removing the charge-offs from the original creditor (at least, not those original creditors) - it will remain as a derogatory account for the full 7 years post DOFD. You can try, after satisfying the collection, to send Goodwill letters to the original creditor asking that they update the charge-off account to reflect a 'PAID' status, but it will still remain a charge-off and negatively impact your score. It will, however, look better upon manual review of your credit reports if it does note that the debt was eventually paid after charge-off - your logic is not flawed.
5) Your plan to go about removing collection items is solid. We can give more detailed advice for each step if you are able to provide the DOFD for each account - same goes for that PayPal loan.
6) You need to let one of your current, open cards report a small balance of less than 8.9% of its limit. You are being penalized (scorewise) for having no revolving credit usage. Never let all cards report $0. So I'd throw a small charge on that Discover card (less than $44.50 which is 8.9% of $500) and let it report, then pay it in full. Repeat this every month. Alternatively, you can actually use the card and pay the balance down less than 8.9% before the statement date. The card will report the balance of your account as of the statement closing date. If you want to get a third card, you can, but it's not completely necessary right now. You can certainly wait until you make some headway with your collection items. How old are the two active cards?
My #1 tip: Try to stay optimistic, remain diligent, and practice patience. This will seem like a very long journey and you will probably have some incredibly frustrating and discouraging moments. Keep posting your progress (and setbacks) here, ask quesitons, and read others' posts - there's a ton of support in these forums. You'll get there.
Re: tmr
Wow thank you for this informative reply! I really appreciate it. Following all the steps you listed. Response to questions:
1. I signed up and pulled my report from https://www.creditchecktotal.com/:
FICO Score 8: Experian 551, Transunion 559, Equifax 558
Factors hurting your score: Serious delinquency, High credit usage, Bad payment history, Few current accounts
Factors helping your score: none
Is there anything else I should be looking for on here? Not sure if I should cancel this service and/or sign up for one of the two competitors you listed.
2. Adding DOFD to each account:
-Chase 1 - $10k - Collections Agency - ARS National Services Inc. - DOFD: 6/2017
-Chase 2- $18k - Collections Agency - ARS National Services Inc. -DOFD: 6/2017
-Citibank- $2.1k - Collections Agency - United Collections Bureau, Inc. - DOFD: 8/2017
-Capital One- $750 - Collections Agency - GC Services - DOFD: 7/2017
-Paypal Loan - $1,380 - Not showing on credit report. DOFD: 12/2016
3. I am in New York State. Looks like the Statue of Limitations is 6 years. Not close on any accounts. 
4. My reports are only showing charge offs from the original creditor. I am not seeing any accounts in collections or collections accounts listed (do not know why).
5. Okay awesome. My biggest question right now is: how long do you think I should wait to hear back from the DV letters before contacting Collections Agencies to try to settle accounts?
6. I will do this. The age of the two active cards:
Open Credit Cards:
Discover - Credit Limit $500 - Balance $0 - Opened 12/2011
Nordstrom - Credit Limit $500 - Balance $0- Opened 7/2016 - has 2 Late Payments on record
Thank you for the encouraging words. I have to admit there are times when this seems like a lost cause. Going to do what I can!
Hello Again,
Glad you got your scores.
1) So, that 'high credit usage' reason code for what's affecting your scores...
Q: Are your charge-offs still showing a balance due?
If they are, then that would mean the original creditor still actually owns the debt and only assigned collection efforts to a collection agency - which is why there are no separate collection accounts showing up on your reports. This is actually a good thing - less work to resolve. First, contact each original creditor and confirm that they still own the debt and it has been assigned to the collection agency from which you've received notice - sometimes the debt gets reassigned and there may be a delay in your receipt of notice from the new assignee. You want to make sure you are paying the right people.
You stated you received settlement offers from the collection agencies -- so, after confirming the collection agency details with the original creditor, contact the collection agencies and settle the account asap. Since they've only been assigned the debt, they will notify the original creditor that the account has been paid and this will lead to the official closing of the account and a notation that the debt has been settled. The balance will then be zeroed out on your credit reports. You can also take it upon yourself to notify the original creditor after payment, but they probably won't make a move until they receive confirmation from the collection agency. This process can take 30-60 days but you will likely see decent score increases from this action alone due to the utlization reduction. See, right now, (if I am correct in my assumptions that balances are still reporting) the accounts are showing a balance against a $0 credit limit, which means your utilization percentatage for each account is over 100%. That is a major score penalty on top of the ding for having a charge-off. Additionally, the creditor can continue to update the account with a negative mark every month if they choose - further dinging your scores. If you catch it now, you will stop additional account updating of negative marks, zero out the balance, and prevent the debt from being purchased by a pennies-on-the-dollar debt buyer who will then own the debt and place their own collection account on your reports. You'll still have the negative impact of the charge-offs, but their effect on your scores will begin to fade over time - and your scores will start to rise in spite of the charge-off accounts (though they will still be held back from reaching their full potential until after the accounts drop from your reports). Once they are all paid and updated on your reports, you can begin a Goodwill letter campaign to see if it works out. Like I said before, success is rare with original creditor charge-offs - but you never know, I've seen success stories so it is possible.
2) Pay your paypal loan -- either in full or settle it. Just because Paypal doesnt report it doesn't mean they won't sell it to a debt buyer that eventually will.
3) With regards to the DV letters, I'll let Robert provide a more definitive answer as to how long you should wait for a response - -he is extremely knowledgeable in this sort of thing. I would say no more than 45 days but... wait for him.
4) You have some age on that Discover card -- good. After you settle those charge-offs, start using it (don't use it just yet as I recommended before because it will only add to your high credit utilization).
As for the Nordstroms card -- start writing goodwill letters to HQ to see if you can get the lates removed from your reports. Pour your heart out to them - be honest about what you've been through and how you plan to rebuild and progress in life going foward. Goodwill letters work when you pull at the heartstrings. If your first letter fails, send a second... and keep going till you get the response you want.
5) Your choice of a FICO monitoring resource is entirely up to you. All 3 mentioned will serve its purpose. Personally, I used (and still use) Experian CreditWorks during my rebuild because it provides a daily score and report for Experian (updates 3am PST) with monthly scores and reports for Equifax and Transunion for $24.99 / month. My credit was changing so much during that time so having a daily update for at least one of the bureaus was super helpful -- especially when I was expecting a change to my reports; being able to see the results of a positive change immediately was also pretty thrilling. Plus they have a great m0bile app. But it's really up to you. I only suggested credit check total initially because they offer the $1 trial 
