This is a long revived post- I'll add a little tax pro insight from what's happened in the last 2 years The IRS went from < 100 engineers on staff who were qualified to audit cost segregations to a few hundred. 

The city where you invest determines all long-term income characteristics.

Take your time and don't let FOMO distract you from your long term goals. 20 years from now, it won't matter whether you bought a house this year or next.

I own a duplex that was built in 1989 and has had 2 stable long term tenants with no interest in selling.

Hi @Frank Pyle,**I am not affiliated with any of the companies mentioned**To secure long-term financing for your Airbnb, look for DSCR lenders that accept pro forma income instead of requiring 12 months of rental history.

Used houses in the area sell anywhere from $75-125 a square foot.These are long term rentals that I do not plan to sell.I am reading the Rental Property Investing book and implementing the method that focuses on cash flow and that strategy states you need to have $300 cash flow per month, per property.

I think if you are going to keep all three parties involved as owners of the deal long term then you need to separate yourself as a renter and a contractor.

Also, he can do the above deal or two or three, all day long now that he knows how to do it and has me help analyze the deal and market.This hit his personal life just right. 

The key is to ensure the HELOC doesn’t turn into a long-term financial burden if the partnership doesn’t pan out.

Hypothetically, if I found a property with strong rental demand, the income could cover loan payments, operating expenses, and generate a modest positive cash flow.While this example involves upfront risks, the idea would be to leverage my father’s expertise as a contractor to minimize renovation costs, boost the property’s value, and create a long-term asset that appreciates over time.