What works well for me in my market - small ranches with minimal rehab needs that sell right under 300k.

If I did two separate units privacy would be minimal and I would need a different set of licensing agreements since it would be a multi unit and not a single family short term rental.

Minimal regulations.

No magic pill, just plain old cold calling. 

And often times tenants are willing to keep renting with minimal upkeep if they just don't have to move.Now before the property managers in the group come rushing for my head let me just say in addition to being a developer and builder of multi family I have a property management company for the above mentioned reasons. 

When we've bought via quitclaim it has only been where the amount of cash we had to put in initially was minimal to help mitigate the risk and the property was under contract for a significant discount.

However It is very private living arrangement than you would imagine.Generally these tenants don’t socialize with roommates, they are hardly in the common area, they are always in their rooms or go out to hang out with their friends or whatever they do. it’s minimal hassle to the landlord.Or this could be just a rosy picture painted in front of audiences in the meetups.

It is what it is, you have to decide what you want to do, if you want minimal cash flow but decent return after mortgage paydown and appreciation the IE is great. 

If it’s a very minimal flip under 20k in rehab cost we can just write you a vacant policy and transfer it to an occupied policy once completed.You will NEED to receive a certificate of liability insurance from your contractor listing you as an additional insured. 

But allocate the proceeds so that one of the purchases uses maximum leverage and other property uses minimal or no leverage.