I've got a few systems at work, specifically for 800MHz trunked systems.
Unless you have a __really__ strong signal outside the building, __really__ low loss coax (or extremely short run), and a really high gain donor antenna, the losses in the system will negate the benefits.
If you are looking at a high rise building, you will likely need more than what you expect. A single antenna at the top of the stairwell isn't going to get very far. Trying to add more antennas will require splitters, and each one will drop your signal by more than 3dB.
To make these things work well, you'll need to have antennas inside the stairwell spaced out pretty well, not just one at the top.
You'll also need some amplification, both directions. Once you add amplification, you'll be adding filters. You'll also have to have some way of automatically shutting down the system if it begins to self oscillate. If the system does start to self oscillate, it will destroy coverage for the radio system over a very wide area.
Since you'd be taking someone else's signal and amplifying it, you'd need to have the system owners permission, or at least make sure they are well aware that your system exists and how to contact you in case it starts causing issues.
Many cities/counties are starting to add these systems as a requirement into the building codes. Often they will be required for new construction. They usually need to be built/operated with the cooperation of the agencies that the system supports (Fire, PD, etc).
If this system is intended for first responder use, I'd really strongly recommend you talk to the department about this.
Then, talk to a company that has designed, built and operated these systems before. They are not something that you can do well without the proper experience and test equipment.
For a couple of high rise buildings, you'd probably be better off looking at a fiber optic based system with a centralized head end. That can save you a load of money in coax, gives you better control, and might let you use existing fiber optic cable that might already exist in the building.
Take a look at these guys. We've been looking at one of their large campus systems with a centralized headend and fiber based distribution. Not cheap, but for a couple of large buildings, it might be what you need:
Coverage - Cobham Wireless