More syntax makes things harder, but the amount of hardness introduced by the craziest syntax is dwarfed by the rest of hardness involved in introducing a type system. It's like saying "Steve was able to walk 20 miles, because his driveway slopes down a little". It may be true that his driveway slopes down, and that may make that stretch easier, but other things are more important.
More syntax makes things harder, compiler that have not been designed wit this goal make things harder. You can look at the papers trying to get this stuff in to other langauges and there are some problems, dylan [1] was doing it befor most others, now rust is coping that stuff.
Actually some of the coolest stuff was done by David Moon (Common Lisp, Dylan) he greated a langauge spec that he calls PLOT [2] and it has a very inovate macro system. For anybody that is intrested in that sort of stuff I highly recommand it.
[1] http://people.csail.mit.edu/jrb/Projects/dexprs.pdf [2] http://users.rcn.com/david-moon/PLOT/ and http://users.rcn.com/david-moon/PLOT/Moon-ILC09.pdf