Try this.
1) Build a coolodor. You'll need a 120 qt cooler. Walmart has them for $59.99. You'll also need a couple pounds of 65% heartfelt beads and a couple small battery operated fans. For less than $150 you'll have a cooler capable of keeping 600 or so cigars perfectly humidified at a stable temperature.
2) After you build your cooodor, every month buy 3 months worth of cigars. In 3 months, you will have nine months of cigars set aside. Three months worth will be in perfect smoking condition provided your coolodor is set up properly.
3) Go to step 1). Lather, rinse, repeat.
As you build your stash of daily smokes, start buying some better cigars and bury them at the bottom and ignore them for at least 2, but preferably 5 years.
Once you have a supply of yard gars, I'd recommend you start buying at least one box of sleeper cigars a month to age. These need to be quality smokes, not bundles. Consider Padron x000's, Joyo De Nicaraguans, La Aurora's, Don Pepin & Jamie Garcia rolled cigars, Oliva's to name a few With a few years of age, they begin tasting just like the much higher priced premium cigars.
The best cigars to age are the med/ful to full flavor cigars. Maduro's are also great cigars to age. Aging has a way of balancing and mellowing strongly favored cigars. Mild cigars aged more than a year or so will lose most if not all of their flavor. Also, keep in mind that a chitty cigar aged for 3 years is gonna taste like a 3 year old chitty cigar.