Let's start this discussion with a rather important link: Pirates Prospects 2014 Payroll
One of my favorite parts of Pirates Prospects are the tools Tim puts together like these. What Tim has done is add up the expected salary of all the contracts the Pirates are currently locked into and then subtracts out any special deals like the money Houston is paying for Wandy Rodriguez.
So the Pirates currently sit at an estimate of $63M that will be out of pocket spending for 2014 payroll. This does not include the $5M to $10M they are pretty much guaranteed to pay in extra salaries. That's essentially guys going on the DL and players moving up from AAA to replace them. Or moves like this year where Phil Irwin was moved from AAA to the majors and straight to the 60 day DL to open a spot on the 40 man roster. Let's meet in the middle and say if no other free agents are signed the Pirates would spend about $70 out of pocket on payroll in 2014.
How much do the Pirates have to spend? The minimum number if we take into account extra ticket sales and new television dollars (although Neal Huntington did state they do not know how much that will be yet) we could assume is $90M. If we are being realistic the maximum is probably $100M and for the purpose of keeping things simple let's stick with these parameters.
That leaves between $20M and $30M (probably closer to the $20M) to get a 1st baseman, 5th and possibly 6th starter, and at minimum a backup shortstop. I left right fielder out because I think there are at least reasonable short and long term options there.
So what is the point of this? Well there were many complaints about not extending a qualifying offer to A.J. Burnett (actually more in the media than on here) and how it was a no-brainer of a move. Well if you sign Burnett to that deal, and it may be fair based on market value, that could leave the team with $6M to get both a first baseman and fill out the bench. That basically gets you Garrett Jones and a replacement level shortstop. Now if the budget is $100M you definitely have wiggle room but maybe not by mid-season to make a trade if you spend it all now so I think $95M is probably the max for the off-season.
Now a little homework. You have $20M to $25M to fill all the Pirates holes... what do you do?
EDIT: Link: Jon Heyman's Free Agent Value Guesses (this is a good benchmark for each player and what a writer, an agent, and a GM think each will receive)