We sound like the start of a bad joke:  A retired attorney, and two Property Insurance guys walk into a bar... 

We have a deal that we've both walked and we like the potential and here is what he'd like:Twelve percent interest only, no payments for 6 months, and two points.

I'm a contractor here in Indy specializing in plumbing, electrical, tile floors, custom tile walk in showers however I offer full service minus HVAC. 

I walked up to the property to take a peak and the neighbors were out on their porch and they asked if I needed help with anything.

In addition, you will need to collect sales tax/occupancy tax, if you do not and get caught, you'll be responsible for the tax. 

I don't think I've been to REEN WEDNESDAY, AUGUST 176:00PMREAL ESTATE WHOLESALE / FLIP / SELF-DIRECTED IRA WORKSHOPSSelf-Directed IRA And Real Estate Basics31 Investors goingAnother Meetup by Ryland in FRIDAY, AUGUST 19 12:00PM PASSIVE CASHFLOW W/REAL ESTATE FOR THE WORKING PROFESSIONALWalk the talk while 'Walking at Heritage Park'Marina Park PavillionA meetup by @Lane K, a great out of state passive income investorREAPS is also a good place as long as that is the kind of community you seek.  

in scenario 3 you can pay tax or do 1031 exchange if you wanted to purchase additional property with the funds.Don't forget you'll be paying 25% depreciation recapture if you sell, regardless of how & when.I hope that helps.Good luck,Joe

What information do I need to gather from the agent / seller, and what additional due diligence do I need to do when evaluating this property versus when we evaluate SFR & Duplex?

I'm gearing up to make my first purchase and I think that my best move right will be to find a 2-3 bed room single family that I can live in personally and rent out the additional rooms.

The two most popular options seem to be using 15% downpayment if buying a duplex or by using an FHA loan that requires 3.5% downpayment plus additional fees depending on the total loan amount.