Vermont or Poconos for Highest Year Round Occ STR

[Louis Zameryka]

People who love ski tell me Vermont is the only way to go in the North East. They are right but it seems that the summer in Vermont might be less demand by the ski areas (less lakes/waterparks). I am concerned Vermont mainly is 3-4 day weekends in winter resulting in something like 30-40 rentable days, with maybe some summer occupancy. 

Poconos has ok ski and pools, lakes, waterparks for summer. The ok ski i think can be offset by the NY/Philly demand from novice, first time skiers or people going to the indoor water parks etc. So even with inferior ski the demand should be there. Then with summer options seeming more plentiful and again the demand driver cities, I can see getting about 80-90 days occupancy better (between winter long weekends maybe a couple of holiday weeks, and 4-6 summer peak weekly rentals). 

Anyone have some advice? 

As far as the deal. This will be my first one. 

I am thinking of 3-4 bedrooms (I do not want too many renters in the house like groups of 14-18). 

I would like to find a home that is close to turn key or to find already furnished places (majority furnished)

I have $50-$60k to put down (or invest upfront with closing costs and rental prep (paint or design/furnishing etc)

My goal in investing overall is to acquire enough cash flow over the next 4-5 years to retire and live off it. Approximately $5000 net income a month would be sufficient. Appreciation is nice but building that salary replacing cash flow is much more important. 

Any advice? Thanks