Lets talk about it for a second. Street is our meal card - as long as we don't die and as long as we keep access to street, our success is merely a function of time. The former is not only a matter of being passive though; don't forget that our first stint had us thrown into middle of a zombie horde. It is quite possible that we will be thrown next to a monster or a natural disaster or even in a world experiencing some kind of world ending event, to say nothing of worlds having unfriendly physics(i.e. Facelessness). As such it is imperative that we get ourselves a baseline defense that can handle most of thing we can reasonably expect to face. Luckily for us, Masks are capable of providing number of get-out-of-jail bailout abilities and Viscerality should do wonders for our ability to survive stuff(having backup bodies would be neat).
For the later, there are three ways we can lose access to street, aside from dying. Losing our opportunity to walk out, breaking some unknown rule and losing access and Street having some kind of limit that we might reach(i.e. 10k trips). Similar to avoiding death, we can avoid this with Viscerality and Masks - with Viscerality we can make it so we can't get knocked out and similar, and then just have a couple of Masks that would facilitate our escape so we can avoid capture. For the rules, there might be things we could do that would have Street close to us. Perhaps getting infected with some disease, or touching the cobblestones or any number of things. The solution to this is to be careful and slowly grow to understand the Street, either by using masks to gain understanding or by talking with other people we find walking down the Street.
Finally, the finality of Street. Rather, the idea that "Street walk might at some point end". In general we don't like our reliance on the Street as we don't understand it - thus our goal is either to understand the Street until it becomes a reliable tool we can just use as we wish, or to create our own means of traversing multiverse so we are not stuck with Street's own rules. This would be sort of a endgoal for us I suppose. But that's for much furtherer in the quest than we are right now; for now we should focus on obtaining Viscerality without fucking dying.