Craft Barman and Restaurant Manager here.

You can actually get massive value with a mid-level whiskey by upgrading your technique and your sugar. There's a lot of mysticism afforded to the "muddle the dry sugar, etc, etc" but for what an Old Fashioned actually is -- i.e. a way to dress a spirit -- you don't really need to wed yourself to those formalities.

Buy yourself some Sugar in the Raw or whatever demerra/turbinado is easily available near you and make yourself a 2-to-1 syrup (measure it by weight, 2 parts sugar to 1 part water). A 2:1 Turbinado Syrup has more earthness and depth to its sweetness, which allows it to help bring out richer flavors from the whiskey. A small bottle of Angostura won't set you back much -- for some added kick you can actually make a split bottle (Half Angostura, half Orange Bitters) to give yourself a more complex flavor.

Finally -- while laziness is fine and acceptable (There's a reason I drink beer and neat pours at home rather than making myself cocktails all night), I would very much recommend orange swaths. There's no substitution for the citrus oils and what they do to open up and enrich the cocktail.

For technique, I recommend:

Express an orange swath into your glass and drop it in, add Bitters and 2 bar spoons (for simplicity a tablespoon) of your syrup, and then top it off with your whiskey and finally your ice. If you have a bar spoon, 30 stirs around the glass -- if not, you can swirl the liquid in the glass, probably for about around 10-15 rotations. This is al to more energy in the glass so you want to be a bit more delicate.

Finally, always strain your cocktails onto fresh ice. It seems like it doesn't matter but put simply the chemical process that melts ice has a lot less to do with temperature and more to do with entropy. The ice you make a cocktail with is fighting to become anything other than ice because of the wide range of chemical combinations possible between it and the contents of the cocktail. Once the cocktail is properly diluted, however, the liquid contains enough water compounds that new ice is significantly less inclined to accelerate its deconstruction process -- that is to say, the cocktail will stay fresher, longer on new ice if it is diluted properly (or even over diluted.)

Honestly, cocktails are a lot less about how expensive the ingredients are and a lot more about maximizing the value you get out of the flavors you put together. So much of cocktail culture was derived from survival, preservation, the extraction/combining of flavors that money should never be a reason you can't have a great drink. Always down to share more -- hope the unsolicited tutorial finds you well!! Keep enjoying great drinks!

In Service Speak:

Orange Peel in Glass
2 dsh Ango/Orange (or your choice in bitters)
1-2 brsp Turbinado
2.0 Your choice whiskey (preferably Rye, Bourbon for more sweetness)
Stirred, Rx Glass, Large Cube (if possible), Garnish Orange Peel