Personally I've never seen any valid reason to transplant more than once.
I go from 7-10 days in solo cup straight to final 20 gallon fabric pot.
If I didn't have so many worms and beetles then I would just plant germinated seed directly into final pot even if it were a 4' x 8' bed.
My root system fills the 20 gallon pot in no time.
If you have a proper soil or coco then there's never a problem watering regardless of pot size.
If your soil is heavy and lacks aeration then you're going to have a problem whether its a 1 gal or a 100 gal.
If you're going to bottle feed then just plant a germinated seed right into a 5 gal bag of coco and water the whole pot daily with 1/4 strength nutrients from day one.
If you want to go organic soil then use the largest pots you can manage, no such thing as too big.
But I wouldn't use less than about 15 gal fabric.
In LOS you want your roots fully colonized with mycorrhazae asap, multiple transplantings retard that process.
Use a coots mix with proper aeration, add cover crop and a few worms plus thick mulch and water pretty much daily at 5% of soil volume, so for a 20 gal pot water daily with 1 gal of water preferably oxygenated. A large plant in flower may need two waterings a day if in less than 20 gal pot.
Watering problems are due to shit soil tilth which results in lack of oxygen to the roots not pot size.