Yeha, when we'll need it is when automation replaces most jobs, and that will also be when something like it can work. If farms are automated and food is delivered with little human labor, the "UBI" is really just a method to track resources rather than a welfare system.
You'd of course need a universal medical care, which will be cheaper with nurse practitioners following advice of AI's. Some sort of system like Gates proposed to tax the robot/ AI's job as if it were a person so the business is still paying income tax for the role rather than just a person.
The UBI would replace all welfare/ unemployment/ everything else systems (Yang says to make the UBI/ Freedom Fund "opt in" and doing so would remove these other benefits for the person). Those that worked for extra money would be more heavily taxed on the money they make, but would still end up with more in the end since they get the UBI also.
You don't need to worry about car payments, because soon you'll have a subscription to self-driving Uber cars and car ownership will be hugely taxed and largely niche.
No need to change the rate base on people living in a city that is expensive. You don't have a right to the city when you're not working anyway. Creating sprawling metropoli with cheap housing would be easy if the people didn't have to live in the big cities. If they want to live in NYC, they can supplement their UBI with a job to afford the payments.
Mostly though, there's no way to "dabble" in this in my opinion. You need to hand the keys over to Skynet and change society all at once.