As far as price deals, your local sporting goods store has often sales. I lately have seen only 170gr .30-30 remmington around. I try to buy 150gr remmington cor-lokt. It seems myself and people I know, the 150gr bullet tend to group better overall than the 170gr ones.
Reloading is not for everyone. If you do not shoot often, you can buy a lot of ammunition for the cost of intial supplies. If you shoot a ton, get some reloading supplies. 1000 rounds of .30-30 can be loaded for about 400-450 dollars. 1000 rounds new is about 750. It will take about 1000 rounds to break even, besides buying initial rounds or unfired brass to start with. I like RCBS's starter kit I have. I have purchased plently of boxes that were on sale for about $12 a box. A local mom n pop gun shop can get some ammo and put it aside for you IF you pay upfront. Find a reasonably priced place with friendly people and try to purchase from them mostly.
Also, you could just buy from a major catalog and wait until they come in from back order. Cabela's has a good reputation and is very honest with it's backorder times.
Your 20 yr old ammo is fine. If the ammo is not in the best shape, you accuracy will suffer a bit, if any. Ammo can last a long time. temperature fluctuations, excessive mechanical vibrations (like leaving them in a trunk of a car), and humidity can effect the performance on the powder (moisture and grain size). Whether you want to reload or not, save some if not all your brass.
With the policitcal mood towards guns and their severely poor financial shape and spending habits, purchase a good 22lr rifle and buy several cases of bricks. My opinion is their going to tax the snot out of ammo and their going to over regulate and require product liability insurance for gun shop owners. Your 20 buck box of 22lr may be 50 in the future. Those liberals think you only need 5 rounds for a hunting season, besides they don't want you hunting in their little picnic basket happy valley anyway.