I think you are totally right about being in a loop - that is definitely what it felt like this morning.
Here are the last few days, I've been keeping track for a while now... Thanks so much for taking a look at it, I really really appreciate your help. I can't quite remember all of the naps that I needed to resettle for... but I think safe to say any that are over 1hr30, as he is like clockwork with length of naps
TUE
nf - 2.00am
awake - 6.05am
E - 6.15am (4min)
A - 6.05-8.25am
S - 8.25-10.10am
E - 10.15am (10min)
A - 10.10-12.50pm
S - 12.50-2.05pm
E - 2.20pm (7min)
A - 2.05-4.10pm
S - 4.10-4.20pm (in car)
A - 4.20pm - 6.40pm
E - 6.20pm (5min)
Bedtime - 6.40pm
DF - 10.00pm (3min

)
WED
nf - 12.15am (8min)
nf - 3.38am (10min)
awake - 6.10am
E - 6.15 (4min)
A - 6.10-8.30
S - 8.30-10.00
E - 10.10 (6min)
A - 10.00-12.30pm
S - 12.30-2.25pm (resettled)
E - 2.30pm (4min)
A - 2.25-5.10pm
S - 5.10-5.40pm (in car)
A - 5.40pm-8.00pm
E - 6.30pm
BT - 8.00pm
DF - 10.30pm
nf - 1.20am (3min)
nf - 3.10am (12min)
THU
awake - 6.05am
E - 6.05am (12min)
A - 6.05-8.30am
S - 8.30-9.50am
E - 10.00am
A - 9.50am-12.00pm
S - 12.00pm-12.45pm (in car) *will wake as soon as car stops
A - 12.45-2.55pm
E - 2.00pm (4min)
S - 2.55-4.30pm
BT - 8.00pm (tried settling from 7.00pm)
DF - 10.00pm (4min)
nf - 10.49pm
nf - 1.15am, woke 40mins after this and I resettled
nf - 5.20am
woke - 6.05am, managed to resettle without a feed until 7am!
TODAY
awake - 7.05am
E - 7.15am (6min)
A - 7.05am - 9.30am
S - 9.30-10.15am (unable to resettle, felt like an UT nap as he will usually go back if still tired)
A - 10.15am - 11.30am (out & about)
S - 11.30-11.40am (in car)
E - 11.40am (6min)
A - 11.40-1.45pm
S - 1.45pm until... here we are now! He made a noise at the 45min mark and has hopefully gone back into another sleep cycle
WRT that 10min CN, If he falls asleep he will wake up thinking he has had a full sleep hence the long A time there. He wasn't showing any tired signs so I just tried him for a sleep after 1hr45, and it took about 20mins to settle him.
The whole day feels like it's been thrown off from that and the 45min CN at the start of the day, do you think I should just go for a early BT after 3hr A? Or is that pushing it? He usually seems to be able to handle a longer A time in the evening... Or maybe he just doesn't want to go to bed!