This is actually several questions conflated together, masquerading as a ‘yes’ or ‘no’ question.

“Can”

Feasibility - is it even possible?

Cost/benefit - is the upside worth the associated downside(s)?

Viability - once it’s done, can we live with the aftermath?

“you”

Could be misleading, in that the most appropriate person to handle this may not be the one fielding the question.

“do ___ [task]”

This provides a solution, which ideally is the expert’s job to provide.

What should be provided is the need to be met.

“by ___ [date]?”

The work has three parts:

Appetite - how much effort are we willing to put into this? Here, we’re associating a maximum cost. We have to consider all three parts.

Estimation - how much effort is required to meet the need? We have to consider all three parts. We only care to answer this to the degree that we’re happy it can or can not fit the appetite. Once we determine that, stop.