02. 400+ weeks at 1
03. 8th year end 1
05. 8th Wimbledon to be won (has this year / next year, he has 2 opportunities)
12. Oldest ATP Rank 1 (record held by Federer at 36yrs 10days 10 months)
14. Longest gap between 1st year end 1 and last year end 1 (12 yrs ..nadal)
11. Most HC Titles (record held by Federer [71 titles] ... Novak is on 67)
I think he'll get all of these. If he wins Wimbledon this year, he'll very likely jump to number one again and will be in pole position to hold it through the end of the year. The hard court titles record feels like a formality – he's always going to play on hard way more than anything else and it would require a massive fall for him not to win 4 more titles, even if they're all rinky-dink ones like Astana.
06. Aim for a 4th US Open (this year is his best chance) DONE !
07. Aim for a 3rd French Open Title (this year is his only chance) DONE!
10. Try for 7th WTF Title, very hard but no harm in trying
I think each of these, on its own, is quite doable. I wouldn't bet on Novak winning all of these titles again, but he certainly has it in him to peak at any given event.
01. 25+ Grand Slams in total
04. Need to beat Alcaraz, Rune & Sinner in Grand Slams a few times over the next 2-3 years.
08. Break Ken Rosewall's record of oldest GS winner @ 37yrs 2 months
09. Attempt at Connors's 109 titles record (low priority)
13. Longest gap between 1st slam and last slam (17 yrs ... held by nadal)
These are a little tougher and further out. To beat Rosewall's record he'd have to win, at the earliest, US Open 2024, right? (I think Wimbledon be a hair too early.) I imagine Djokovic will still be contending by then, and probably beyond, but I also wouldn't be terribly surprised if his last major ends up being something sooner. And as far as beating the Little 3, a lot of that depends on everyone making the date. Not sure he'll meet all three enough to have any sizable slam rivalry with them, but we'll see.