A good point to take away from @Colleen F. is that depending on the type of deal and age of property you might need to spend a chunk of time there occasionally handling larger capital improvement projects.

His 2 brothers were roofing contractors, and he would occasionally help them. 

Krab keychain as well that you flash occasionally

We even occasionally see Conex boxes used to increase rentable SF. 

You can find deals on MLS occasionally but generally the sellers there want retail and as an investor you don't buy retail.

It does result in occasional short periods (typically 1 night but occasionally 2 nights) that a unit goes unrented because with the fixed fee our single night charge is not cheap.  

I think where the lines are blurred a little for me is that this is a friend of mine and we don't have anything "official", he's just an investor himself and we talk about real estate a lot... and he sends me houses sometimes.

If you want the condo as a place to visit occasionally, then that's very different than looking at it as a pure investment. 

Occasionally we revisit to negotiate. 

We get an occasional one, haven't found any big discounts but they seem to keep dropping the price about every thirty days in our area.Picked one up recently, was on the market for 90 days price drop of 10k about every 30 days.