You've got your fall back plan in case everything goes to hell in a hand basket so you're covered there. Your second 'civilized' property is what you seem to be agonizing over. If I were in your shoes I'd go with the least urban possible option until it comes time to head to the sticks! Of course I've never liked city life anyway and have always gravitated toward more remote areas whenever possible so I guess my advice is biased.
Its the kids causing the agony.
MichelleO and I would gladly just take off and leave the city but city Life offers classes, friends and other resources to my children they just can't get on a 100 acre property in the middle of no where, and I don't want to take those things away if I don't have to. Right now, we think we see the oncoming wave, but nothing all that dramatic has happened to us personally yet. I am still very gainfully employed, and the understanding of the collapse just isn't mainstream yet - and probably won't be till they are forced to call a bank holiday. Hell they still call it a recession instead of a depression. And when it does hit, it hard to predict how bad it will get. In Argentina, there was an increase in crime, but not really a big change mortality rates. You had roadblocks, and gang territories, but you were robbed and beaten, not killed. People did not really band together.. not even extended families ( can you get along with your relatives for a week at Christmas?) A gunshot would scatter crowds, not cause firefights. Still, people go to work, and play and shopping.. Of course, in Argentina, the population had more knowledge of and ability to survive in that scenario, was not nearly as well armed, and didn't throw the entitlement spoiled brat temper tantrum I expect to see in this country. I think we can expect lawlessness to appear and go unchecked - encouraging more of the same. The police just won't come to some areas, and which areas those will be is hard to predict, nor will they be willing to engage whatever gang has control there. They will just file a report and leave. This is already happening in up-dollar Palm Desert outside of Palm Springs, and it will only get worse. It will give the Fed an excuse to impose Martial law - and then travel between my properties may become difficult or impossible - not to mention the possibility of criminal setting up roadblocks on the way - the highway bandit will be back.
For the last few years we have been prepping and I have just written off the current house as useless, and loosing the money in it was a shrug ( it was mostly borrowed and bubble money anyway) but if I get the AG land in town I suspect my attitude will change and I will care about what happens to the property. I will want it back if I lose it somehow to squatters, etc as things recover. (of course I may have the same problem up at the Teotwaki place) and it becomes a prepping place as well, so a lot more of my effort/fiat may go into it, making me way less willing and more painful to abandon it when the time comes. Of course- we have like minded (but unprepped) friends in town, who may, if things get bad, be willing to try and stay and defend the place as it offers a better chance of survival than their little suburban home.
As MichelleO said to me this morning - "We are spending money like its going out of style-- because it is" - but its still not clear to me where to best spend it. Its a good problem to have, and I am lucky to be blessed with such resources at this time, but I don't want to squander them.