I'm going to give this another spin.
Always think of resale when you are buying. Most people don't; they get too personally attached to "their "house,whether it's beautiful or a piece of cr*p.
My advice is given being on my 5th house in 2 states. All sold in 3 months or less, 4 of them during recessions.
OK. As another poster said, you cannot underestimate how much time home remodeling/repairs take. The house I am in now had to be totally rehabbed: roof, doors, windows, outdoor landscaping, 3.5 baths, kitchen, paint inside. Then, there's the upkeep. This is time away from riding.
Are you willing to live in a house that is not what you want inside? We thought we could, for awhile, but our house was totally remodeled inside within 9 months. If this isn't important to you, then it's a different story. For a lot of people I know, those plans to remodel never happen.
So, while house #2 has the acreage,it's not really what you want. And, when thinking of resale, how important are those trails you are going to build, to other people? I've seen several examples of things that were personally important to homeowners (the most obvious being elaborate pools/spas/backyards) that are actually liabilities when selling. Again, you might not be thinking of resale now, but sometimes this stuff hits you in the face, later.
Last point. DS just bought his first house. He was lucky to get a state subsidized first time buyer loan, but with home prices the way they are around here, he was outbid on every decent house he and DIL liked in the more "prestigious" areas. So, this is what he bought: a totally rebuilt/rehabbed 3 bedroom 2 full bath Cape. Stainless appliances, hardwood floors, woodwork from 1905 saved and prominent in the living room/dining room. A sun porch, a finished full basement, with a work area/studio for DS to do his music and DIL to paint. Boiler room big enough for the washer and dryer plus tools and 4 bikes. Downsides: on a very busy street in a close in suburban city that's traditionally more blue collar, plus home to a well known university. Schools not so great, but not the worst, either. No driveway, garage, have to park on adjacent street. House is high up on a steep hill, with 50 steps up to the front. Has a large amount of side land and a back yard. Front yard is a steep slope that is terrible to cut the grass on. Bus stop to almost anywhere one block away, close bike ride into Somerville, Cambridge, Boston. Oh, and very near (but not next to) a major highway. You can hear it and probably see it in the winter.
DS and DIL overbid the asking price by about 6K. They were about 500.00 over the closest bidder and got the house. There were tons of young couples wanting to buy this house, despite the obvious negatives. Why? Because of what my son says... the other houses were just pieces of sh*t inside. This house was walk in ready. The came to us with hesitation about putting a bid in on the house and we said "do it." They are used to living in the city and dealing with parking. And they can slowly look at how to fix the slope, parking, etc.
They are very happy and their friends are very jealous.