A few thoughts.
For the cost of shipping your bike there and back you could definitely buy and insure a bike in Europe. AnTyx can help in Estonia, I've helped a guy in the past in the UK, and by all accounts Ireland is quite a straightforward place to buy (UK no longer in EU, complicates it slightly, technically you are only allowed 90 days out of 180 in EU). You don't need something the size of a monster BMW to tour Europe, the roads are fine and you'd be OK on (say) a 650 with luggage.
I prefer GPS over smartphone - I find the screen larger, brighter and clearer. Routing in cities can definitely be a headache so some sort of nav is a big advantage.
Theft can be a problem in the big cities. Find secure parking if possible, be prepared to lock it and don't leave luggage on the bike overnight. Out in the sticks no problem.
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