I believe you are better off having one multi-way splitter instead of a daisy-chain of two way splitters. You will get less signal loss using a four or five way splitter once than multiple two way splitters. You also need to make sure the frequency response is high enough (up to 100,000 Mhz I think). Boosters may not work as the signal has to go both ways for internet, converter boxes, etc.

Quality of the cable can make a difference too.

Quick solution - put a two way splitter in the closest location and see how it works. If no problems you are done.

If something stops working, look at a different solution.