The problem is that we're looking for properties that will either appreciate or at the very least not be a loss on resale. Her program is 4 years and there's nothing in Guelph for her after that time - we'll be moving...again.
While we definitely don't need a big place, smaller places are no cheaper and are going to be harder to resell. The first one concerned me only for the pool and the vinyl (the flooring doesn't bug me at all) - it's my favoured option. I'm worried that if the vinyl is near its end of life, then the cost of replacing same will be on us.
The second one concerns me because it doesn't show quite as nicely in terms of upgrades - the kitchen is fine for us, but for sure we'd have to replace the appliances at the very least (and no built-in microwave is kind of a bummer for counter space). Also, no builder would want to take the house since flipping it would be a tough project for the reasons you explain (re opening up walls). That, and it's a bit further out than we want. If the roof is in rough shape, well, there's another what, $6-8k spent? Guelph's market is so hot that we can't try to reduce the purchase price for those things.
These are all going with zero conditions (incl home inspections), some are entirely cash deals.