As someone who has moved greater than 20 times in my life, owned and resold 4 houses, and am in the process of doing it again, I have some experience in this stuff.

Let me preface this by saying that we DID buy the fixer with land out in the country. Guess what? Logging trucks, gravel/mining trucks, harley riders and even cyclists who clearly feel the need to YELL to each other to communicate while riding have turned our idyllic peaceful dreams into a non-reality. And NO ONE would guess that our road is that noisy or busy from just a few visits. We live on a prime cycling road (every time we mention where we live, cyclists and motorcyclists always know it) so we thought that this house was perfect for us. It was the perfect size, liveable but in need of some updates/renovations and the property was small but plenty of room for what we wanted with the mature fruit trees, wide open space for a huge garden, room for animals and work buildings...etc. And compared to what else was on the market at the time, it was a dream home.

In reality, all that stuff/land/visions just took away from cycling and other things we wanted to do. 1 acre of lawn, full of gardens and fruit trees takes 3+hours to mow...every weekend. My drive to work is ~40 min each way so I've lost a lot of time there. I can't really justify biking to work as that's 1.5 hours each way and who has that kind of time to spare on a regular basis. And our fixer house is 40+ years old and has cost us upwards of 75K in renovations/repairs (things we often didn't plan like dead tree removal, chimney/wood stove repair, roof replacement that was ridiculously expensive due to regulations (ie, not something an inspector could have known), plumbing issues, etc) in the past 4 years.

So even if you don't factor in the time and cost of caring for our livestock, this particular house is a massive time and money suck that we had not anticipated...at all.

Now we are looking for something in town with almost zero yard and no external maintenance to do. Having the idyllic place in the country is still our dream, but the plan is to do it when we retire and we have the TIME and motivation to do it right.

I agree with others that resale always matters. When we bought this place, we thought it was going to be our last house (unless we won a lottery that we never even play!). Even so, we still considered resale things like size, amenities and commute distance to where most of the jobs are around here. Those things should make it possible for us to sell it once we find the new place. I've seen other homes in our area (comps, for sure) sitting there because they have only one bathroom, no garage, crumbling roofs, or ugly kitchens and bathrooms...but I don't think we'll have the same issues because we paid attention when we were buying (and we fixed everything!).

So my advice? Don't be lured by the house in the country unless you are willing to accept the lifestyle change that it may require. As someone else pointed out, the devil you know is often a lot easier to deal with. That said, do you need to buy now? I can say that 'settling' can be really tough. The problem with picking a place that has a known downside is that there may be other downsides that you haven't even considered. Add those to the one you know about and you could be miserable (or regretful) a lot faster than you might think.

If you don't have to buy now, I'd say to keep looking. At least, that's what I'd do...