There really isn't a rule of thumb here. You need to know how strong your signal is at the input of your receivers with various levels of splitting. If you have a very strong signal, you can certainly use two or three passive splits. However, if you have a weaker signal, you should probably use an active splitter with a narrow bandwidth. The second part is very important, as you absolutely do not want undesired signals, such as adjacent TV stations, amplified as well - they'll only serve to desensitize your receivers (especially if they're lower end models with poor filtering inside).
Now I remember where I pulled those numbers from, the Shure stuff on antenna distribution and placement. They say that 5dB of loss is about the maximum acceptable level. A passive split drops 3dB, so a second passive split would be 6dB and opening the door to problems. If you then have say a 10m or more coax run between antenna and receiver, then you need also to consider the loss caused by that cable.
Amplifiers mounted to antenna can help to overcome cable losses etc. But you can have too much and sometimes less is more.
Wideband v Narrowband - It's all about the right tool for the job. It may be that you are running a substantial number of systems and hence need to have systems on more than one band, then you will need a wideband splitter. This given Log Periodic antennae or Helical or other such wideband antennae. But if you have that many systems, the better option would probably be to use a wideband as the primary split and then run all the secondary splits with narrowband. Best of both worlds then. Of course if you are needing this sort of number of systems, you really need to be using high end systems which will have decent filtering built in...