I'll need to make a few assumptions as I try to answer that question ... but, you can adjust them to match your exact situation First we'll look at the cost and revenue assumptions
Property Price: $500,000
Mortgage (assumes 30% down): $1,700/month or $20,400/year
Property Maintenance: $2,500/year
Property Utilities: $2,400/year
Property Insurance: $600/year
Property Tax: $5,000/year
Property HOA: $3,600/year
Property Management Costs: 50% of rental (they find the renter for you ... do it yourself at VRBO.com)
Number of ski days (days resorts are open): 155 days
Number of ski days rented (75%): 117 days
Avg. ski season rate: $500/night
Gross ski season: $58,500
Number of off-season/summer days rented: 90 days
Avg. off-season/summer rate: $150/night
Gross summer season: $13,500
Gross Yearly: $72,000
Net (after $36K Prop. Mgt): $36,000
Net (after $14.7K expenses): $21,300
Net (after $20.4K mortgage): $900
You could save a considerable amount by managing the rental yourself (using VRBO.com) and hiring maid service to clean up (a lot of folks charge renters a $150-$200 cleaning fee in addition to the nightly rental rate).
I also have a spreadsheet I've put together that can let you do 'what-if" scenarios. Just call and I'm happy to send that to you for free and with no obligation.
Let me know if you have questions ... and ask about help with your closing costs when you call.
Equity Real Estate Luxury Group