If you're expecting property owners to sell their home to you at a discount, you'll need to earn their trust - whether that be by demonstrating a successful track record with purchasing/selling similar deals OR by meeting them face to face and separating yourself from the dozens of local investors and realtors.Lastly, I'd recommend searching past posts related to this topic as well as checking out books related to your target investment strategies.All the best!

I think this is especially true in the context of current alternatives like the stock market, which trades at 30X price to earnings (a "3.3% Cap rate") or 1.6% dividend yield, bond yields which are far less tax efficient, and private businesses, which are far more active. 

We all know what goes on in bathrooms and what kind of extra care they need.

As long as you stay invested and let your hard earned capital continue to grow, you can pick your spots when a real estate opportunity offers outsized returns comparatively to other investments. 

It's not fool-proof, but I think odds of earning 7.5% using a barbell strategy in the average year on your money is 97% likely with very very little effort. 

After five years, I am willing to buy the other owner out or they could stay in and continue earning and enjoying the property. 

I'm considering converting the shed into a DADU to maximize the use of the space and earn some extra income. 

Like maybe I could pull enough out from heloc on primary residence to pay off debt and then rent out my primary and use the extra cash to payoff heloc and then do another heloc once the original one is paid off.

The reality is the opposite - if it's not in writing then the PMC doesn't have to provide the service or can charge extra for it!

It shows you are serious and willing to go the extra miles to make it work.