Space or bragging rights?

As the home hunt continues - you always have to struggle with compromises. There never seems to be a clear path and you can never refine the situation to reduce the complexities. Everything always seems to be a mess of cascading dependencies. The latest struggle is looking at two homes... Candidate #1 I call the Bragging House. It's got all the things you'd ever want to show to your friends when they ask 'what did you buy?'. It's got the beautiful yard.. it's got the landscaped hillside.. its got a good sized lot.. it doesn't have houses backed to it.. it's well maintained on the inside.. it has a full sized bar in the basement. Not a little wet bar.. a full on 8ftx5ft type thing. Then you go out back... A pool... hot tub... built in grille... pool deck, wood deck.. and still up the rise, a children's playset and area to play. Check it out So what's the problem? Jump like crazy! Well - the house isn't really quite what we were looking for. It's a bit small to stay in long term.. the basement isn't that large.. the upstairs rooms are ok, but not great. Basically the house itself structure wise (rooms, space, etc) is good, but not great. You don't have room to do new things.. anything you'd do you'd be ripping out something to do it. No media room.. no game room.. not even a true in-law suite. It's a house that has probably reached it's peak.. and apparently the homeowners think so as well as they've priced it pretty high. But on the pricing front there are comps to show it can be lower. There is ammo out there to counter their asking price. It's been over a week and its not under contract, so likely we aren't the only ones wondering about the price either. Candidate #2 is the diamond in the rough. Let's just get the ugly out in the open. It's a short-sale. It's been vacant with various stages of renters in and out for ages now. It appears sound, but needs new flooring throughout the middle and upper floors, paint, and the hardwoods look pretty disgusting dirt in groove wise. It has at least two significant water spot areas that need investigating on ceilings. The outside has been neglected... the deck needs refinishing... etc. However, it's a monster. It's one of the larger models you can get in the neighborhood.. it's over a 1,000 sqft bigger then #1 just on the upper levels. I think there is probably another 500-1,000 sqft extra in the basement (the numbers published don't seem to all add up). The kitchen is massive... it has a sunroom that was bigger then my entire old kitchen+dining room combined. It actually has a separate office, plus the 5 bedrooms. It has all the structural checkboxes that we were looking for, plus more. I don't know what I'd do with probably half the space to start with... but there is room to do more for many years to come. And it's listed at 550k. To put it in perspective.. that is almost 70k less then #1. It's probably 100k less then the nearest 'like' house and even further below what a great condition house of the like model. It's a 650k-750k house.. way out of my budget... for 550k. The unpolished stone... the diamond in the rough. However as things can't be easy.. there are the compromises. #2 is on a smaller lot, with 3 homes around you. There is trees and screening.. but they are there and you see them. Compare this to #1 which at least behind you is pretty much a private kingdom... except the fact on the otherside of the castle walls are a major road.. which on the otherside will be commercial development. #2 has a reasonable sized yard, but in a odd shape.. but plenty of room for the kids to play. The whole thing needs major TLC to look top shape though.. while #1 looks like it could be on a book cover. Neither property is on a culdasac which I would have preferred.. but #2 is at least in a dead-end area. Neither property properly backs to trees with nothing behind you. Neither property has the big open lot (tho few exist in our community). One property you are buying the outside... One property you are buying the house and minimizing the outside. One property you are buying a polished stone, the other a rock if you hold just right, you can see the shine. One you move into a confined space... the other would be like moving into a warehouse. Crazy.. nothing is simple. What would you do? Well yesterday we started to put our money where our mouth is.. and wrote an offer on one of these two. Which do you think it was?