Thrifty or nifty?

This post is about choices: choices that you might make every day or once in a decade. But every choice is important, so here's my dilemma: do you choose to pay more for a quality item or get smth less, well how should I put it, well-fabricated or lower-grade and save money? I usually make the latter choice and suffer the consequences (yeah, the car I picked out was real cheap and broke down a week after I bought it etc), while Erik  tends to spend more money (even if he doesn't have it) but gets an item that he likes and that will generally last quite a while. I feel like the last year has been a good lesson for me: I had to make a few pretty important decisions and here's what came out of it.
#1 I bought a car. Yepp, for the first time in my life, I all by myself, spotted this yellow VW bug with great mileage and price, and insisted (I'm using a pretty mellow word here) on getting it. Since our old van started having heart attacks, my husband gave in and I drove it home. The thing broke down a week later. I had it fixed. And then it snowed... A two wheel drive with little weight and bald tires on ice... Man, that was one morning ride to work ! I still like my car but I would definitely never buy it. Nor do I want to drive in in winter. Even for really cheap:)
#2 We were blessed with free flights to Hawaii. Two weeks of vacation: we haven't had that since our honeymoon! So I set off to find a good (cheap, that is) rental in Kauai where we were spending the last 8 days of the trip. Erik took care of the first part and paid a little more than I wanted but the place in Maui he picked was beyond anything we expected. So after staying there we land in Kauai and drive around the island for a while. Finally it's getting late and I pull out the directions to the condo I rented (and paid in full for, got a great deal!) on the internet. We roll up to a two story building in a shabby residential area. "oh, we are just like the locals" I say, "this is gonna be great". I get out of the car and look up into a tree under which we parked: it's covered in cobweb. Well, I guess I'd better not stand under that tree for too long, I figured, nevermind that we rented an open-top Jeep.  I set off up the stairs and around the verandah to look for our condo. O'k then I had to duck my head and freak out for real: there were all sorts and sizes of spiders all around the building, on the rails, roof, BBQ, windows etc. Some of them were 3 inches wide! Just hanging there all perched up as if they were ready to get me. I ran inside with Erik coming up behind me. We called the owner of the rental, she said smth like "the spiders won't hurt you, that's a tropical island, they are not poisonous bla blah blah". Hippie, I thought with swelling bitterness deep in my heart. Then I looked in the bedroom area and saw a huge gap between the floor and the door with the bed right next to it. I think I started crying or smth, cuz the next thing I remeber we were checking in at Best Western for the night.
So the moral of the story is: I think I made a few bad choices which led to more expenses and turmoil than expected. But who doesn't deserve a second chance? According to Erik: his wife. Ding it, I just saw this great deal on a car... Would be perfect for snow!