The market has not fully re-bounded to the point that would make it a great market for flipping unless you are investing in Columbia County.

First question have property values started to rebound there?

You dont hear of tornadoes, earthquakes floods in this area just a boom town for autos that went belly up and that happens to buisnesses all the time. then they rebound.

Prices haven't rebounded all that much though.

My partner and I have a 20 unit in Gillette and have noticed a slight increase in vacancy but are able to attract new tenants with waiving half of the deposit or breaking the deposit into 4 payments and sometimes a 50% on movein month.Gillette is way more hit by the oil decline than Casper, but the price of oil has rebounded from $28 to over $50 per barrel as of today.  

Unfortunately, these are the kinds of areas that are not going to rebound without a lot more help from local business, philanthropists, government entities and outside companies that we may not even know about yet.  

As they say with no risk comes no reward, also considering you are young you have a higher risk tolerance and can rebound from any mistakes that you may make.

Should I always assume the market will rebound?

Other than just spending the next year saving, is there a way for me to get to that 30% quicker so I can go in before the dollar rebounds?

I don't feel that Newbugh is yet on a rebound, so it may be a cashflow headache to own property there right now.