Unfortunately I was not able to put much away for retirement most of my life so I was thinking about attempting to buy 4 rental units over the next 4 years with the hopes of building up something that could generate income in 5 to 7 years to supplement my retirement at 68.

Additionally, Airbnb income during this period could generate steady cash flow, though market conditions and regulatory risks should be considered.

After 45 + years as a real estate investor, broker, lender, fund manager and syndicator, I’ve become aware that the “dream” of many investors and investor “hopefuls” is to be able to generate enough cash flow to live off their real estate holdings and accumulate enough wealth to make “work” optional.

They are designed particularly with mother-in-law or next generational living in mind.

You're absolutely right—positive cash flow from rentals can vary significantly depending on factors like property costs, financing, and the ever changing market conditions.For real estate the challenge isn't just accumulating properties but creating a framework that builds net worth more strategically and sustainably.Cash Flow can be generated in many ways, my intention was to better understand the investor mindset and their approach, if they wanted to share.Based on your example, if using conservative calculations at $100K/door, you would pay $20M for access to $40K/month. 

I am glad you highlighted the management piece as this is a crucial part of buying in another market.Excited that you are stabilized and are generating cash flow on that deal. 

Just know that it is a "no days off" kind of business and very mechanical.I would suggest documenting your process via video so that eventually you can bring people on to replace the different hats you will be wearing.Keep in mind of these 5 components of any wholesale business.lead generation, deal sourcing, underwriting, marketing, transaction coordination.

Here is some clarification:When property inside of an IRA is financed, it generates UDFI (Unrelated Debt-Financed Income), the income derived from the leveraged portion of the property. 

It gives you access to funds at a relatively low interest rate, and you can repay it as the rental generates income.

During this time you are not generating any return from the money invested in the ADU.