I know we talk about this topic often, but I'm starting this new thread in order to consolidate the discussion:

1. Airport arrivals
a) don't use Didi or private drivers because pickup is far more painful than spending 10 minutes in the taxi queue
b) SHA
i. if your destination is on Line 2 or Line 10, the subway is probably faster than a taxi, but Line 2 can be really crowded
c) PVG
i. I love the #2 bus a lot, and if you are staying in true Jing'an (as opposed to "North Jing'an"), it is a no brainer
ii. But, I tend to take taxis now because the bus doesn't work for me, and we're only talking about $30
iii. The Maglev is certainly worth trying for tourism value, but is unlikely to save you time or money

2. Airport departures
a) Didi works pretty well on this front to both airports, but I would still take the #2 bus from Jing'an if convenient
b). the subway is often a good option to SHA, but not so good for PVG

3. Subways
a) if you care about getting a seat, Line 2 is not your friend, but the more recent lines are
b) pick hotels with good subway access
c) download the explore shanghai app; it's honestly nothing more than a subway map, but having it installed saves time

4. Shared bikes
a) this isn't a year round solution, but if you happen to be 500 meters from a subway station, and the weather is okay, grab one
b) IMO, Mobike is a little nicer than Ofo; there isn't much point in signing up for both

I did a DiDi pickup once from PVG and it seemed straightforward enough. I wonder how it's more painful than waiting for a taxi if there's a designated pickup area.

The drill works fine if there are 5 or less people waiting in your chosen pick up area, but it's a bit of an adventure during busy times.

Paying for it, or using without payment?

While I realise that even Mobike and Ofo offer free options if you jump through hoops, I'm cool with paying y1.

I often fly into Pudong on an international flight and need to make my way to Hongqiao to take a train to Nanjing.
I have tried every combination and find the bus (30RMB) to be the "best" alternative in terms of cost and time to get there. However, there are often a lot of people meaning that you can't get on the next bus, resulting in a wait in excess of 30 minutes. If the waiting line is too long, I take the Maglev + subway.
If I wish to connect to a very specific train (some high-speed trains are faster than other), I take the Maglev + subway. While it may or may not be faster then the bus, the travel time is 100% predictable and I know exactly at what time I'll be in Hongqiao as traffic has no impact on travel time.

I've found the Maglev to be a pretty good option when staying in Pudong along Line 2. Taking the Maglev to Longyang Lu and then Line 2 to Lujiazui is generally faster than a taxi, particularly if arriving during busy traffic hours.

Taxi v Maglev/subway to LJZ is a random walk IME, but I generally prefer the former because: 1) less walking and waiting at PVG; 2) Line 2 can be miserable.

If I use didi at PVG, are the drivers easy to find? Also, would they be easier to find if they were luxe vs. the more normal didis? I'm paranoid about not being able to find the car.

Get a taxi.

The drivers are fairly easy to find, and the app has a built-in translator so you can still communicate with the driver even if you don't speak Chinese. The pick-up area for DiDi if you're flying into Terminal 1 is a pick-up area at the elevated outdoor parking garage.

I was get my taxi at PVG through didi so I can pay with my credit card

If the meter shows 201 rmb for a ride from the end of the Maglev train line to Jing'an, and the driver drops you at the side of the road instead of at the front door of the hotel, I'm guessing there's some sort of trickery going on?

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Definitely. Taxi waiting at Longyang have a bad reputation.
Any taxi that drop you on the street rather than pulling up to the hotel entrance is up to something no good.

I figured as much since our taxi last night from PVG and our taxi today to Wild Animal Park were both about 200 each.

Out of curiosity, what's the best way to handle this when it happens?