BUT the fact is people who don't do any homework are speculating and gambling and often motivated by laziness and greed.

If you want to gamble on appreciation, I would say buy a property in Boston.

DC market is an appreciation play, and while I know everyone won't agree that is just a gamble, almost everyone I know that bought in DC have enjoyed their property values, many, many, many years later.

Appreciation is in my opinion a gamble and often times people want the steady cash-flow of investment properties when building their portfolios so they can step away from there full time or part time jobs.With that being said, I am an investor and also invest in the NE Ohio Market and have had upwards of 250 units in our portfolio and continue to purchase here.

Looking for info, good advisors, your experience to protect properties

Some investors with vast portfolios that already throw off great cash flow will buy properties such as in New York and gamble that it will appreciate through speculation.

But of course there isn't the income coming in usually...unless maybe you put a billboard or cell phone tower etc on it.. and there are taxes to be paid. well I grew up in the land business so that's what I know.. today everyone is brain washed with it has to cash flow and appreciation is gambling.. so be that as it may.. yes I have done very well with land and determining where I believe markets may go.Plus I was a top producing RE agent so I really did not need cash flow .. what was 200 bucks a month going to do for me..

I just want to make sure that me "taking the tax hit now" at a lower bracket makes sense versus sheltering as much as possible for a "gamble" that I can do Roth conversions later and pay less/no tax. 

It’s also an appreciation play which is somewhat gambling.

I am sure that a ton of people will jump on me about saying that property prices will go up as being gambling, but look at the chart @Amit M. posted... it is straight up accurate.