As a bourbon drinker who also enjoys scotch I am happy to hear that you are going to give my favorite whiskey a fair go. I hope you learn to enjoy it, though, of course, you may find that you don't much care for it. Whatever floats your boat! However, I am confident that you will find something you like among the many fine bourbons available.
As to what you should try I am not really sure. I don't really know what whisky you like. Smoky Islays? Sherry monsters? Grassy Speyside malt? Also, are you planning to buy a few bottles or bourbon or are you going to be trying things out in a bar or buy minis or some combination of the above?
Anyway, here goes. I think you should try something from each of the major distilleries. Not as daunting a task as it may first appear. There are relatively few distilleries, though you wouldn't guess that from the labels. A good resource for determining where a bourbon is made is StraightBourbon.com's bourbon database. Here is the link. http://www.straightbourbon.com/brands.p ... e=bottling
Here is my basic advice.
Try something from Buffalo Trace, Heaven Hill, Jim Beam and Wild Turkey.
Buffalo Trace is my favorite distillery. Whatever you do, try some Blanton's Single Barrel. Any expression will be fine. It is all good. Gold is probably better than Silver, Silver better than Special Reserve etc. Higher proof is better than lower proof. I don't think I have ever had the 40% abv. If all you did this June was to buy a bottle of Blanton's I would say you had given bourbon a reasonably fair trial.
Other Buffalo Trace whiskies that I think well of include, Buffalo Trace, Elmer T. Lee, Ancient Ancient Age 10 year old. They also make Old Charter in various ages. I have tried the 8 year old. It is a very different bourbon from those listed above. The mashbill is very high in corn, low on rye and barley malt. Smooth and sweet from the corn and the time in the wood. I like it. Oh, and Buffalo Trace makes the George T. Stagg.
Heaven Hill makes an enormous range of whiskey. Evan William's 7 year old is a good, affordable, every day bourbon. Well thought of in the bourbon community. I had some 12 year old tonight. The extra time in the barrel made it a much better pour, IMHO. There are vintage Single Barrel expressions as well.
My favorite bourbon from the Hill is Elijah Craig. I love the 12 and the 18 year old, too. The Twelve is on my "always have an open bottle" list. It is not to everyone's taste, however.
Jim Beam has several super premium bourbons, too. Booker's is great. Very high proof. It varies from barrel to barrel but 63% seems to be normal. Age varies, too. Around eight years old is standard.
Knob Creek is very good, too. 9 years old 50% abv.
Jim Beam Black Label is good, too. Affordable, well thought of. A little light for my tastes. Give the White Label a miss. The Green Label is reputed to be inferior to the Black, but I haven't tried it. Old Crow is a Beam product. I haven't tried it. It is supposed to be pretty bad.
Wild Turkey. Great distillery, great bourbon. Don't get the 40% abv. It is probably okay, but why bother? The 101 proof is much better. In Japan it is 8 years old. In the States I understand that it often contains younger whiskey. There are a number of premium bottlings, too. I love the Rare Breed barrel proof, for example. But the WT 101 is really excellent bourbon.
One more recommendation. The Van Winkle bourbons are very highly thought of. They use wheat rather than rye as the flavor grain. This makes for a smoother whiskey. Rye can burn on the way down. Maker's Mark is also a wheatie. So, if you can't find a Van Winkle you can try that. I have only tried one VW expression, the Rip Van Winkle 10 year old. Love at first sip!
As to water. None for me thank you. My advice is try it neat first then add water to taste.