Sometimes your risk reward changes substantially with the types of projects you can get into for one vs the other.As some other posters have alluded to, time constraints drive a lot - a light rehab/cosmetic buy and hold is possible for navigating while having a 'regular' job - and certainly managing rentals while working is possible as well.The last one, and I'm surprised no one has mentioned this - is market specific. 

Property Specifics: The duplex was purchased in 2014 for around 250k in an up and coming area in DT Charleston.

I don‘t have too many specifics yet, but wondering what the Bigger Pockets Community thought about this?

Cool thing here is the IRS lets you use any reasonable method to allocate between land and building (they call the building the improvement) It’s going to depend on the specific situation what is going to be best for you.

@Bradley Jordan My recommendation is that you ask the 2nd broker to write in specific language that covers your situation.

Check out socketsite.comLuxury condos aren't doing hot in SF and there's some examples on that site that are interesting.I think the key here is that it's specific condos some of which were likely overpaid and now we're seeing true value but it's more of unique situation then city wide trend. 

What about this deal specifically would make you say its best left to local investors?

Ask them if they can fill out your application for your record keeping and sign a new lease with you in which you have specifics as to who / where to send rent, when it is expected and the late penalties.

If he insists, talk to your title co. about specifics.

In addition to your note, with specific payment terms, you need an executed and recorded 2nd mtg/deed of trust.