Hi Neil,
Sounds like you have put some thought into this and want to start off in the right place.
Categories: In your line of thinking you seem to landed on wanting category pages either for organization or for keyword opportunities, which is great. However, without knowing exactly what your categories are, or what type of website you're using, it is hard for us to commit further on this line of thinking.
Dynamic vs Static: Depending again on what type of website you're building or working on and the amount of items you'll ultimately end up with its hard for me to give a recommendation. That said, I do have some general rules I like to follow. If we are talking +100's of properties I would absolutely go dynamic.
Dynamic requires more initial coding to get setup, but once done you end up with a very easy way to add properties with minimal effort.
If you're only listing 20-40'ish properties, you may find that putting the personal touch into each page and going static is a better route.
In the end the dynamic vs static debate comes down to time and reward. If I were selling 10, 50 million dollar properties you could bet your left one, that I would absolutely take my time and do them static. But if I had to list 50, 60k properties and 2 150k's I would spend my time on the back end coding something that allows me to plug and play the stats.. so to speak.
To summarize I used property sales as an example here, but it wasn't quite clear if you were talking about selling properties, or possibly hotel rooms. In any case, using categories is usually a good thing. In the Dynamic vs static debate it all comes down to time vs reward, which is the best way to use your time given the potential return?
Also don't forget about the Schema when you make your decision. https://schema.org/RealEstateAgent
Hope this helps you,
Don