We can't guarantee past our GC that the sub's employees are paid so we rely on hiring a good GC that has reputable subs, contractors, and not a bunch of cash workers.

THEN you have to support yourself while you are working on your first deal. 

Purchase price: $28,500 Cash invested: $121,000 Sale price: $170,000 SINGLE FAMILY RESIDENTIAL fix and flip What made you interested in investing in this type of deal?

Need to keep that cash moving!

Buy box: Location: Approx. 30 min drive to Boston Heights, for workNeighborhoods: Decent walkability score - not far from shops/restaurants/trendy neighborhoodsIdeal tenants: Close to hospitals/universities/schools for professionals/students/familiesBudget: $175-250K - Buying w/conventional loan, 5% down/ approx 20K reno.Property type: MFH 2-4 units - preferably side-by-side, with a yard we can fence for our dogUnits: 3+/1+ - better if 1.5/2 bath per unitTimeline: Plan to live there for 2 years, but possibly only 1 year if we find another investment opportunityGoal: Focus on appreciation - would like to see cash flow in year 2-3 (the year we move out), including overhead (Vacancies, Maintenance, Utilities) and budgeting in PM if eventually we don't manage ourselvesValue add: Opportunity for some forced appreciation, but not a full reno - cosmetic upgrades and updating kitchens/baths while we live in one unit.

I have seen loan products that will let you purchase a mixed use property to live in the residential unit, but that is a specific product and you should consult and expert to see the best option for you and your cash on hand.  

That is important to know as you may have to pay that cash out of pocket.

They sell you the land (you may or may not need to put some cash down) and they carry a note in 1st position.

I threw it into the cash flow calculator and it said it would either even out or it willl have a monthly cash flow of around 300$.

It sounds like you are already leaning towards selling the duplexes so you can retire and have cash on hand.