First, please do NOT think you're going to generate enough cashflow to live off of within 3-5 years. 

A clean U&O means the Seller doesn't have to do anything.The home inspector is a different issue.

Fast forward 20 years when you are 60 and you have a multi-million dollar real estate portfolio that should be generating a solid amount of passive income. 

Guests appreciate functionality more than anything, so as long as they’re clean and do the job, you’re good to go.Little details like this can make a big impact on guest satisfaction.

What you would want to evaluate is the income generated from the income-producing property(s) to see if the income from your rentals would cover the cost of your new HELOC payment.

However, vacancy means covering 100% of the expenses.Multifamily properties almost always generate higher cash flow due to multiple income streams, which also reduces the risk of vacancies.

This is relevant for multiple reasons 1) appreciation is where the real wealth is generated in RE 2) real estate has tax advantages over cash flow 3) in CA property tax increase is capped.  

If you've been active in this business and actively pursuing a profit during the year, the loss the business generates could help offset other income on your tax return. 

Do you have someone that manages it all including bookings and customer service or just specific parts like cleaning only? 

And those also only have a limited ability at best to generate a balance sheet, which you generally want to include on a 1065 return.came here looking for answers to exactly this question, and David is correct re: why.