I want to point out that this comment you quoted took my original answer out of context, I was not referring to the 2005 Subaru, but the OP was asking about buying a 1999 V70 Cross Country.
BTW I went online and 2005 Subaru is still in the bad head gasket years. Heather just bent over at the dealer right before Christmas for a new engine in her current Subaru which was just out of factory warranty. Do the math, just out of warranty 12/2017 makes her current Subaru a 2013 or newer, still having engine trouble. No goodwill warranty at Subaru! After 20 years of brand loyalty to Subaru, Toyota will be getting her business. I tried to get her to look at Volvo but she buys into the belief that Japanese are the only people who build reliable cars (except Subaru now).
You are right a old $1,500.00 car likely will need two or three times that initial investment to bring it to a reliable state. After all a 1999 car is 19 years old. That's a lot of old wear parts alone. Like expensive engine mounts, cooling system parts, not to mention all the potential years of neglect that a unknown service history due to several likely owners resulting in engine sludge, expensive timing belt service overdue, crud in the ABS unit due to lack of break fluid changes, and all the other ways people neglect the maintenance schedule recommended by the cars manufacturer resulting in expensive repairs. June