I think this borders on insanity.Take your cash (and family, though I'm in the camp that thinks kids in Vegas for vacation are not the best idea) to Vegas and gamble in the casino.

I currently have access to two single family homes (375-550K FMV) in Southern VT (one near the NH border) that have 50-100K in equity that I would be able to assign a contract to.

I'm working on a parcel right now that has some old graves on it, is bordered on 3 sides by an old landfill, a sewage treatment plant, and a radioactive waste storage facility, and there are 2 homeless squatters who have been camping on it for 5 years. 2.)

I am not aware of the Santa Clarita option as that is not in LA city of borders...county yes but don't know if those non city areas were part of the LA city proposals or not.

They too could have just kept using the land but they wanted to control it.If it were me I'd be looking to see if I could profit on a resale to a bordering property, regardless of zoning.  

I live in Danbury, but work on the Monroe -Trumbull border as an engineer during the day.

So, depending on how you hold your U.S.A. properties and how you repatriate your retained earnings back into Canada will determine the amount of tax you will pay in either country.Most scenarios are variations of this simplified scenario:  You hold the U.S.A. properties in your own name, and the income comes across the border into your hands here in Canada, the IRS will withhold an amount of taxes in the U.S.A.  

At the time I was also looking at the seaside city of Quincy and was totally surprised to find that parts of Quincy bordering a river were at higher flood risk than some parts quite close to the ocean that were on higher ground.

Now what actually happens at FEMA as they review the individual policy I don't know...Clint said in his post if I understand correctly they would validate against their maps.I have three properties that are along the borders of these zone maps, and I am hoping I can get out ahead with this map change.

Worth checking out (some googling should get you the programs - TD Cross Border Banking is the one I've used personally to handle all my cross border banking needs, although never got a mortgage with them).Hope this helps - I'm sure if you give some more details around what hurdles you're trying to get past (financing, finding properties, property management, cross-border tax issues, etc.) you'll get lots of advice!