Re: 2 - I can't agree. Yes, the trams and trains stop running soon after midnight and start up ~5am or so, however that is pretty good time coverage. Many people in Tallinn don't own cars, and use the free public transport a lot, plus the coverage up to the city limits is also quite good:
https://www.visittallinn.ee/static/files/063/2018_tallinn_tr...
One 'problem' here is that Taxify / Bolt is so cheap. I'll not even think about dropping 5EUR on a fare if it means slightly less hassle / time getting somewhere.