How can I go after a check issued by my insurance for the repair of my roof from a lawyers office?

Unfortunately, this question involves issues relating to the specific terms of the contract for representation that you have with your attorney's office.  In very general terms, it is very typical for attorneys representing clients with insurance claims to have provisions that provide that the check for the settlment proceeds to be sent to the attorneys trust account so that appropriate reconciliation of costs, fees, and allocation of distritrubutions can be made.  Typically this process  requires the funds to have cleared trust before any distribution can be made and for bookkeeper or other staff to update the disbursements for costs, billing records (if not pure continegency), and for a reconciliation to be prepared.  These "back of house" administrative tasks may require input from several different firm staff members and no attorney here on AVVO can do anything more than guess at what is going on, but it could certainly be some benign admistrative hiccup or holdup.  At this juncture, it would be appropriate for you to follow up directly with attorneys office as to the status of the matter.  

While this question ended up in the "Construction Law" category, since the settlement check has already been issued, the better category would be ethics and professional responsbility and this tag has been added. Unfortunately, no attorney on this website can do more than speculate on what is happening in this particular case, however, it would not be unusual for the contract for representation to provided that settlement proceeds are to be deposited to trust and for disbursements to client and attorney to be made after costs are deducted.  Typically, this involves waiting the time period for the check to clear trust (and insurer's checks are often from out of state) and for someone at the attorneys' office to prepare the reconcilation statement which can easily take several weeks.   As two months have passed, it would not be untoward for the questioner to follow up with their attorney's office via telephone call or email asking about the status and suggesting setting up an appoinment to come in and sign the settlement statement and pick up the check.  This may well prompt movement on getting this done (it could be on the desk of a staff member as a "non-urgent" task or somewhere else in the adminstrative process).  I wish you luck.