Finally, there's a strong ethos for living in SFH in my area and a negative connotation with apartment dwelling. 

v=qHpc80xVNFk Dave Meyer in podcast rents out "accessory dwellings" which sounds much easier then legit duplex conversion.

May check with local HUD office also houses for humanity helped a person i met build his own home on same plan.

@Verna Littleton and @Nathan Beach have jumped in and are ready to rock.From our experience with human beings, we always scout at least three other alternatives who can jump in and take over at any given time since we can't afford to slip.

That being said, I would like to reiterate that nothing is going to change.. because, you know.. humans. 

I always end up going by myself so it'd be a blast to have actual other humans to talk to :)

My job doesn't have the best work/life balance and it's something we're hoping to change using the power of real estate.My wonderful partner and I want to focus primarily on multi-family dwelling rentals using a buy and hold strategy. 

You will want a landlord dwelling fire policy and an umbrella policy to increase your liability!

I know the DP (dwelling protection) insurance policies are standard landlord insurance but my agent tells me I can also get a Businessowner policy to cover the property (mostly concerned with fire, wind, standard perils). 

@Adam PetrieIf they are 2 single family dwellings on the same lot you likely need to seperate the lot with having both houses fronting on a public street.