Thing is i am concerned to move considering the fact that millions are unemployed and finding a job in the Real estate industry might be tough.. 

Westchester is a tough market due to the high prices (and INSANE taxes), but there are opportunities.

Even though this downturn still has stopped a decent amount of buyers, the supply of a good MF is tough. 

The fun part is that I teach at an art school where I have some really scary looking, tatted and pierced co-workers who happen to have MA's in theater and wouldn't mind a fun gig over the summer. 

Thankfully my tenants have been able to keep up during these tough times.  

I would ideally buy a triplex or fourplex but it might be tough to find in the neighborhoods I'm considering.

I would imagine he would have a tough time explaining why the property went off the market, then came back on at a higher price. 

If you can get it, do it, but keep in mind refinancing may be tough.

Thats tough since loan requirements tending to keep changing. 

Manchester strong rents, but getting into the market can be tough, as multis are priced accordingly.