I think the younger you are the more likely you are to think collecting HTF cigars is a good idea. One health scare in my mid 40's was enough to change my opinion.
Now a days I give away more HTF cigars than I smoke because I get as much if not more enjoyment from sharing them with friends...
Living in PA is limiting your selection a bit. I can't find Black Bottle on your Wine and Spirits site. It's about $23 here if you find some it's pretty good for the money.
The Black Grouse kind of fits your requirements @ $28.99.
You could also try McCellend's Islay for $24.99.
While...
There is a lot of good info here to help your choose your 2 other bottles. You can glean a lot of insight by reading AVB's reviews, especially the ones you are considering. I keep quite a bit of scotch on hand and still go back to read his notes.
Smokey: Laphroaig 10, Talisker 10. Lagavulin 16 is an excellent dram and without a doubt it's smokey and rich but you may be over powered by the peaty, iodine flavor considering you are a Glenlivet drinker.
Blends:Johnnie Black is the #1 selling premium blend. I really like it and it's at...
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