I purchased a ski condo and there isn't much to take pictures of immediately outside the condo.

I would tap into your 401k as a super last resort.

Its at a ski resort so it seems like it would be time consuming.

In California and Florida there are two State run plans of last resort (Cal Fair and Citizens respectively) for the otherwise uninsurable; properties that private companies have already deemed too risky and are effectively subsidized by taxpayers.

Now there is winter cold and snow but Tahoe ski resorts are 45 minutes  snow mobiling cross country etc.. then the weather in summer is 70 to 85 NO humidity and google the Sierra Buttes  / Sierra City  20 minute drive up to the mountains and 15 Natural lakes full of trout etc..

Today this would be possible in high priced markets were your average loans are more in the 500k range so only 10 a month.. like CA  NJ  Denver and ski areas . 

Today, that building generates enough passive income to cover his annual retirement contributions.You mentioned taking the 10% penalty, which I’d only recommend as a last resort.

We are literally next to a golf course and about 10 mins from a ski place and I don't think fancier amenities would generate a ton of ROI. 

Have they ever been to a public pool, or water park, or hot tub at a resort or gym? 

I also agree that there have been so many syndicators who's deals have dried up and they have resorted to teaching/mastermind as a source of income.