Your friend needs an education fast before he spends much money. Never buy a gun with major repair issues. Best way to figure out gun values is to watch a auction site like Gunbroker and see completed sales. You will see very quickly that 95% of guns listed don't sell and almost all that do sell have no reserve price. That means the seller started them very low and let the bidders decide on what they thought it was worth. Fair market value, for that gun, that day. Set your searches to show only guns with no reserve because they represent almost all of the guns which really sell on that site. By default the rest are priced at full retail or retail plus prices or they would be already sold. You do this by using the advance search feature on the site.
As to brands in the beginning is stick to Sterlingworths, Ithaca NID, Remington 1894 or 1900. LCSmiths are good but often have minor stock cracking issues. Parker are over priced by people who buy the name not the gun, just as Winchester and Browning names on guns. Set your spending limit at 500 and wait until the right gun comes along.
If he likes the Remington 1900 have him look at 1894's also. Little better quality but mostly seen in Damascus. Learn about Twist, Damascus and steel barrels as well as what are safe to shoot shells are for each. These old guns are not to be shot with modern factory shells, they need ammo designed for their period. More 5-7,000 psi than 10-12,000 psi of today's shells. That's ok because reloading 12 ammo is easy and economical still.
And understand all the stories you hear about that great sale someone missed buying don't out weigh the thousands of guns bought for too much that people never want to mention. Often the best thing to do is think about it and then forget about it the next day.
