how long should something like this take? Should the trusses be built on site or shipped in?
Depends how fast the crew is in manpower. Once the prep is done and walls are figured out , if a crane can reach the site setting the truss and sheeting in could be in one day. The killer is the prep and flooring. Hears a rule of thumb in renovation. If you take the time to rough figure the materials it cost to do the job add 2 times that figure for the labor. The $100.00 figure you posted earlier is for NEW construction at best and not re -habs New is a 50/50 in basic cost. 50% materials/ 50% in labor. Renovation for example if its $20,000 for materials then its $40,000 for labor. Again it's a basic rule of thumb and can change either way. Generically use the $100.00 per square and add $50.00 per square to that.
The biggest burn time here is the prep for the truss. I'm assuming you need to rip down or build up the block walls to get them level unless the walls were level and they used a mini sloped wood knee wall to get the roof pitch. It could be both. A 4" block on the facade and 2by wall behind that laying on the 8" wall. More so then not the block are cut in for slope then a formed/mortared cap for roof plate set on that.
If no partial knee walls in wood then the block walls need demo to get level to the lowest point in the block wall. Then a course of 4" solid block cap needs laid and new 1/2' anchor bolts also needs to be grouted in the courses below. The code there may not be easily applied to your situation there. If they require so many inches in depth for anchor bolts and you have 3 core block its extremely hard to get an anchor bolt past the first full course of block. There is compression anchor bolts that can be used in the 4" solid cap but that may not pass code there. If you run into that ask if you can use them in conjunction with hurricane straps to back up the compression anchor bolts. I'm sure Hurricane plates will be required after the trusses are set. They only catch so much from truss to wood plate. If they were extended to catch the top plate and more side to the full 8" course of block wall then they may be a resolution for if if the issue crops up.
I would most defiantly buy truss for a couple of reasons. If you are going to tear off the old roof and expose the structure you need a new roof sheeted in and tar papered as quick as possible. Never know when an isolated rain wants to sneak in. Also you can't stick build a truss as cheap as buying them. Many people don't realize the reason truss use many different designs with smaller 2bys is the truss company use "stressed" lumber. Its not off the shelf at lumber yards. There is actually stress ratings stamped on the side of truss if you look closely enough. The other reason is the truss itself is cambered to "pre Load the truss for weight. I stick build truss or buy them depending on the access to the renovation work. When we stick build we have a couple of choices. Run a ridge board or jig out on ground and use Gussets to build the truss "no ridge board."