Planning a flip of the property with 50k cash buyout + 40k estimate of renovations.We've considered paying cash for property, obtaining loan for 90k-100k and paying ourselves back first before starting renovations. 

Our plan is to start our business/investment there.

My plan involves paying off the first mortgage's judgment amount afterward.

Plan on 25-30% down. 

We are planning to turn our primary residence into an STR at the end of this year and are looking to take advantage of accelerated depreciation if we can meet the REPS requirements.

My outstanding loan balance is 163K @ 3.5%I calculated that I'd clear 900/mo after expenses.I was planning to buy my new house for cash, but with the market where I'm moving/buying I'm having to go about 100K over what I was planning, so I'm taking out a 50K loan for that property.

You won't get the replacement cost if you plan to walk away.  

Many resorts hire seasonal staff that needs housing.All said, if you can acquire well, and your plan is appreciation, Tahoe is an awesome place where real estate is a limited resource.Consider snow removal. 

If he earns a 10% annual rate of return (compounded quarterly) in a portfolio created by a robo advisor, Investor A will need 22 years and seven months to become a millionaire.People gripe about negative cash flow but with this plan you probably can't touch it until 59 anyway.

However, getting from simple Phase I/II due diligence to developing a remedial plan can be a large and complex process and costs would have a wide range until more is known.