Spend your time filling the needs of your buyers, not speculating if you can find a buyer.And, if you'r not actually buying and using guru tactics, then you increased the odds of ticking off some owner, especially if it is owner occupied because you failed to market the place.

(If I speculate, the price of the house is estimated to go up 2% by next year so I may be able to come close to breaking even on a sale, but again only on speculation so I'm not counting on it) I should be able to rent it out and break even if I manage the place myself.I know I don't want to invest in Massachusetts long term.

Working in the real estate business and investing or speculating are very different.

If its negative, you need to be sure you can cover that shortage, which often comes in big lumps.There is also a speculation play with real estate.  

One is a bank owned property in Florida - 3 bed, 2 bath - where we're able to get into it for about $140k and we're doing a little speculation that it'll go up by about $50k in 3-5 years and we should be able to get $200+ in cash flow.  

I suspect the owners are trying "speculative vacancy", letting it deteriorate (lower taxes) and hoping the location will appreciate over time until a greater fool drops by.

The only other 'rescue' on these properties at these prices, is that if you believe you are buying in a good market, and that the values will increase, then you can use these properties to 'speculate' - you may be slightly cash-flow-negative, but if home prices go up 10% or 20% and you are leveraged, that will make up for your negative operating income.

My wife and I are starting to look in LA, but it feels insane and overpriced, with mostly speculation driving the market.

I do aggressive land speculation in affordable housing.

That is how a investor would view your property and why it is obvious you are simply parking cash on a speculative venture.