There was some speculation a few years back that it was heading in a much better direction and there was building and improvements being made and businesses moving in.

Highly speculative and risky but, it is a strategy.

Is this speculating, timing the market, or simply a good investment in a depressed time? 

Ask them what your options are, it's all speculation until you talk to them.3.

He doesn't like debt or bankruptcy for personal reasons because he was an over-leveraged real estate speculator that couldn’t liquidate his assets fast enough when the bank called his loans at the bottom of the market, leaving him with millions of dollars of debt which resulted in a rough bankruptcy for him.

If someone hasn't, then it's all speculation.

Now most GP try to do refi and buying time so to speak, in speculation that Fed would reduce rate to 75 bps.

But that's just evidence based speculation, just a guess. 

I do very little speculative investing.

If you are interested in speculating market appreciation in the Triangle, S.