I'm assuming that can be employed for all safek situations
Echo chambers are boring and don't contribute much to deeper thinking and understanding!
I don't want to give a rule for all without a more thorough review, but if there is a specific one you are asking about I can review. The bridges between Brooklyn and Manhattan are all okay.
I believe many would walk those on shabbos, I would think that might be a ק"ו to not say tfilas haderech there..How about gwb and/or Whitestone, are those tefila eligible?
Rabbi Berkovits says Tefillas Haderech between Y-m and Bnei Brak/Bet Shemesh/Tel Aviv/North etc at the turn off to Bet Shemesh. He says it is the only area along the route you can say it at. If they take the 443, he says it in Shma Koleinu the Shemoneh Esrei before (assuming he knows in advance), otherwise without shem and malchus.
GWB can be walked on shabbos. I need to check Whitestone.
Forgit who I heard it from - on the 443 you can say it as soon as you get to the neighborhoods of the chayos ra'os baderech...
Perhaps there are cholkim but RYBs apparently does not agree.
It is more complicated than that according to R Shlomo Miller and others. You need to know where the city ends to know where to start counting and you would measure that similar to tchumin.
Do you do ריבוע for תפלת הדרך also? I was always under the impression that it is after the distance from the last residential area using the road you are on.
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