Nothing seems to cash flow even positive and with many saying the appreciation market is softening significantly in the next year or 2, it seems pretty impossible to find a solid deal that will carry through a possible looking correction without destroying me.

The housing has softened definitely there will be a short squeeze to come there's tons of damaged homes...I'd say rent for now and next year when everybody forgot about this mess and has rebuilt consider buying.If you can find a distressed seller then be ready to deal with faulty foundation, mold, flood damage.  

I was hoping that they might soften a bit, come May.

Nobody really knows how much it'll affect the local student housing, but it'll obviously soften the market a bit.  

The best remaining incentive, the 2-year ownership tax-free profit, is great, but if the market softens with fewer buyers, there may not be much profit to worry about saving taxes on, anyway.          

There hasn't been a huge correction but there's been softening for sure.

Though, if you just want the cash and plan to hold out until the market softens it may be the right move.

I assumed an extremely high CapEx over 18 years (2 washers, 2 dryers, 2 fridges, 2 water heaters, 2 water softeners, 2 dishwashers; 1 furnace and 1 AC unit, and 1 roof).

Making some improvements (especially those that are readily visible) really softens the blow of a rent increase.  

We will keep an eye on the multi-family inventory in MA going forward since if we see a sharp increase in inventory this will be a good forward looking indicator that prices may start to soften.