In that Fire scenario, they could lose all their clothing, furniture, electronics, kitchenware, etc.

One funny thing about the guys is that they would rather buy a new pair of socks than take their dirty clothes to the laundry.

Plumbing issues (upon further inspection... caused by hair extensions and 'do rags flushed down the toilet).A busted clothes dryer (I swear they tried to dry a stack of bricks in there).Anyway... needless to say, that particular property has been a money loser for us.We're now on our 3rd tenant and hopefully, it'll be drama free and we can start going cash flow positive.If we can right the ship, it'll be paid off in about 4-5 years and then we should see some great cash flow (fingers crossed).So what does this have to do with you?

I would also need proof that this is an actual investment, and not a timeshare in sheep's clothing.

We meet at Starbucks after his yoga class.

New electrical is better than real-old electrical with cloth insulation but not as good as 30-40 year old wiring with thicker copper wire and thicker plastic sheathing, so long as the sheathing isn't brittle. 

Bam you are ready.Now when you meet with your client's clothes matter even more.

In general are older, smaller homes really just money pits dressed in fancy clothes?

If the house does what you need it to do and the numbers work, just do it.Using an analogy for clothes. 

Your clothes are an asset.