So many others "settle" and take the deal in hopes for higher sales prices in time, they are literally gambling on continued appreciation to take the deal down.

Don't get me wrong; there are plenty of issues/problems/quirks that old houses have that new houses don't, and an old house can obviously have hidden problems and big repair/maintenance bills too--which is why thorough due diligence is fundamental to REI...but, the point is: a brand new house is not a foolproof solution to repairs/maintenance headaches (and in some cases, a brand new house can be a much bigger gamble than an older house).This is a particularly important lesson for inexperienced investors, who tend to be the most prone to "shiny object syndrome" (the tendency to let nice aesthetics distract from real, underlying issues).

It could appreciate but I consider that gambling.

Even if a car was built in Michigan - if it was sold in Canada you will have to jump hoops of pages and pages of paperwork and fees.Talk to a cross border accountant re your tax situation.Good luck!

I am looking in neighbourhoods that border Sandton, Johannesburg - so Kelvin, Rivonia, Sunninghill, Randburg. 

This borders on a legal question, but I think one can draw up and create their own deed, do their own HUD-1, and take the deed to the courthouse and record it without an attorney or title company.

My question: would any price point make this property a good investment or does the neighborhood it borders negate an incredible price? 

After a phone call with the planner, it turned out to be OK.The second obstacle is the property is located in a flood zone border.

Even if there's a small chance of getting caught, I'm not going to risk 18 months in the clink plus big fines and having my loan called plus ruining my creditworthiness just for a lower rate personally, but I'm not a gambling man. 

You hopefully won't lose much in that gamble but that is what all tax liens are, a gamble.