I'm not a fan of real estate plays. But isn't the thesis for SRG pretty simple? Sears is paying below market rents. Eventually, these assets will be re-let at market rates. A bit similar to buffett's real estate near NYU?
HHC might be more attractive, but the thesis is more complicated.
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That may be a concise statement of the SRG thesis, but it glosses over significant complexity.
Both SRG and HHC are development plays that will stretch over decades. So, at a very high level, what's actually easier to assess: (i) the effects of a potential SHLD bankruptcy and estimating demand and "market rents" for Sears-type assets sprinkled all over the country over the next 10-20 years, or (ii) whether, over the next 20 years, there will be continued demand for housing and office/retail space in Honolulu, a high-end Houston suburb (which is entirely controlled by HHC), a very high-end Las Vegas suburb, and a small city midway between Baltimore and DC, along with continued demand for access to the South Street Seaport?
I think (ii) is actually easier to understand and assess than (i). I'm not saying HHC will definitely turn out to be a better investment than SRG. I'm just surprised that people interested in long-term development plays aren't more interested in the company that appears to have much better assets.
EDIT: Also, regarding your Buffett example, aren't HHC's assets more like being "next to NYU" than the Sears/SRG assets?
And you may be right that all real estate plays are somewhat dubious, because the underlying return to investors depends in part of how fast the assets are developed, which is impossible to predict accurately when you're talking about developments/land sales over decades. But given that fact, isn't it even more important to favor the assets that are most likely to continue to appreciate over time ( e.g., oceanfront land in Honolulu, South Street Seaport) versus real estate assets in flux (malls)?