To quote a classic:
[Y]ou’ve got to decide if you can deliver a Fortran compiler from scratch in seven days. You’ve got a staff of two programmers to help
you.
Can you do it?
“Well, I suppose, it depends,” you say.
On what?
“Um, will my team be able to use UML-generating tools?”
Does that really matter? Three programmers, seven days, Waterloo
Fortran IV. Are UML tools going to make or break it?
“I guess not.”
OK, so, what does it depend on?
“Will we have 19 inch monitors? And will we have access to all the
Jolt we can drink?”
Again, does this matter? Is caffeine going to determine whether you
can do it?
“I guess not. Oh, wait. You said I have a staff of two programmers?”
Right.
“Who are they?”
Does that matter?
“Sure! If the team doesn’t get along, we’ll never be able to work
together. And I know a few superstar programmers who could crank out a
Fortran compiler by themselves in one week, and lots of programmers
who couldn’t write the code to print the startup banner if they had
six months.”
Now we’re on to something!
If your team has worked together before, if you set your features to match your deadline (not the other way around), and if you have a keen sense when you've gone off the rails, probably. Presume you can, multiple your estimates by four, and carry on!
(Seriously, I can't answer this technically becuase it's a people question. But I hope it's inspirational! Good luck.)