Offer to do it over a period of time to "help him transition".

I have enough funds available on the side to finance this transition for about 5 or 6 months assuming no surprise expenses. 

Over time, I've transitioned more into the real estate finance side of things, but having a solid background in construction is in valuable.   

@Jo-Ann Lapin  flipping was definitely my goal when I took on this venture, but I have transition into learning  and knowing how to buy and hold instead.

It's hard to stand out.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

They wouldn't even let them hang curtains, so this should be an easy transition.

It's hard to stand out.There are some owner-occupied segments with people who share motivating factors for selling their home.Seniors with Long-time Ownership: often ready to downsize or transition to assistance.Homeowners with Low Financial Stability Scores (FSS): Struggling financially and likely ready to cash in on their asset.Both these categories have additional advantages in that they probably don’t haven’t been updated and may have deferred maintenance.

“That’s why the Downtown Austin Alliance is partnering with the Austin Board of Realtors and 30 other Austin nonprofits and business organizations to advocate at Austin City Hall for a new land development code that provides enough transit-supportive housing capacity.”

I have always thought that one day I'd transition into a RE Agent.

If you're in a "not so great/hasn't transitioned yet" neighborhood, section 8 is the right choice.