You've clearly illustrated how different our personalities are.
You seem to be more conservative with your investments whereas I am more of a risk taker.
I would take the expensive properties EVERY time and build them up as fast as possible.
Yes, you spend more initially but man, it's so easy to crush an opponent once they land on your decked out properties. I love scorching my kids when I play with them.
It does teach them valuable lessons, though.
Also, strategically, when you own the end of the board many players really count on that extra $200 when they pass go to top up. If they are struggling in that home stretch it can really be the final nail in the coffin.