The Dalmore produce a scotch specifically to compliment fine Cigars - The Dalmore Cigar Malt. It may be in the budget....it goes well with cigars but it's not really a great whisky...it's ok, but there are much much better.
If he likes the sweet smokey flavour of a good Cigar and wants to start with something similar (and would live up to a cigar at the same time) then I'd suggest going straight for a plain old Ardbeg 10 year old. Wonderful, and well under budget.
There are better Ardbegs which are more expensive but probably not a good place to start, they are a little more acquired
Another good punt would be a Lagavulin 16 year old - again a very high quality smokey dram.
BEWARE: these are Islay malts and are very flavourful and smokey, so if this isn't what you think he's like then steer clear for starter/newby as they can put some people off.