The sidewalk that the Product Manager is walking on, is paved with trade-off dilemmas. Avoiding one will usually force you to face another, and eventually you'll step on them all.
You Shall Not Pass!
"I want it all and I want it now!" Queen sings and probably had in mind the biggest trade-off dilemma of Scope vs. Time.
We are the gate keepers, the doormen who let features inside and then shuts the door behind them. We set the point in time, we put the foot in the door and say to all the rest "you shall not pass".
Add to the mix Product Quality and Cost, which are additional extremely important factors in this equation, and you got yourself a nice matrix of trade-offs to handle.
The Here and Now
Taking a step back, to the phase in which the roadmap and the work plan were not defined, and strategy is still in mind.
What should be the trade-off between addressing present pain-points and pursuing future plans? What is the perfect mix?
The question can even be more complex when the 'here and now' that you are required to address actually contradicts the strategy and direction the product is headed towards.
Low Hanging Fruits
Low hanging fruits are always tempting. Are they worthwhile? More than thorough-comprehensive work?
And on the same note, is it worthwhile building something you know will eventually be re-built or even EOL?
"It Depends"
Well, I won't surprise anyone when I'll say there are no bulletproof answers for these questions. Knowing them would be a good place to start though.
Obviously the common answer will be "it depends", and that's true cause there are so many factors that affect the decision - Internal factors like the company or the product itself and external factors like the customers or the market.
In my mind, the right combination of Analysis, Experience and Intuition will probably get you to the right answer, but that's a trade-off by itself...