Let’s break it down and explore how you might approach this idea, the challenges you could face, and ways to structure a deal that could work for both you and the landlord.Why the Landlord Might Be Open to SellingThey’ve moved out of state for health reasons and don’t have family nearby anymore, which might reduce their emotional attachment to the property.The idea of simplifying their life and pursuing something like sailing around the world suggests they could be open to letting go of the property if it helps them achieve their goals.With significant equity or potentially owning the property outright, selling could provide them with a substantial cash windfall to fund their future plans.However, their belongings on the property could signal hesitation to let go or simply a logistical barrier they haven’t addressed yet.

@Nick Rivers If you've already taken courses and webinars, then the only thing that will help you become more proficient is by actually underwriting deals on a regular basis. 

I make my regular interest-only payments for the first 7 or 8 months, and my interest-only period lasts 5 years.

@Holly Thorsen see above for potential challenges tapping your equity in the rental.You only need 5% down for a regular mortgage, 3% down for an FHA mortgage - so why don't you have the funds?

- If the Association Fees are regularly increasing or the Association is poorly funded - SELL.3) How much of your TIME do you want to invest in all this?

It's easier for an investor to stay committed to the plan and avoid change orders than it is a regular homeowner.

I’m thinks just pay him his regular price for the job and throw him 5-10% finders/gc fee instead of making a 70/30 split or something like that.

I would shoot him regular updates to keep him in the loop.

They should pay just like someone on a regular lease pays - cash or equivalent into your bank account. 

Whether it's a private chat group, email support, or regular check-ins, make sure there’s a way to get ongoing help.7.