If the property isn’t worth 20-30% more after 5 years that’s another reason to sell. 

Not only do you have more flexibility, but you have another set of eyes on the deal, and you won't have to deal with the risk/huge changes to your personal credit. 

Do you perform regular preventative maintenance to avoid emergencies or are you more reactive?

So if you want to increase your equity in the market overall by owning more units (ones where you can increase rents annually), I'd consider buying more if you even have the chance to.

If so they would have sold their house for (ultimately) $75,000 more than they did; received 9% interest (probably as much or more than if they invested the proceeds) on the amount they were waiting for, and if by some small chance the borrower/buyer defaulted, had an opportunity (along with the frustration, cost, etc) of reselling the property and obtaining a “windfall” profit.2.

@Shane O'Neill Let me know about your property in Orlando, I may be able to help you sell it to my investor list.

More than happy to connect with you talk about kickstarting your RE investing and house hacking journey.

You will get paid less on a team, but get way more opportunity.

Yesterday I did my final walkthrough with my tenant and I have to say; it’s more work than I originally thought. 

I am sure the answer is "it depends" hence the term "creative financing" but was hoping people might offer a few examples to help me think more about how i might approach deals where the seller is motivated and the property as been listed for a long time.