Find a good multi-family deal in New Britain, and Owner Occupied can get some good rates. 

I am looking to start with doing small multi-family buy and holds.

So we have been debating a couple options,1) Buy condo/townhouse (possibly without FHA) and then buy single family residence with FHA, move into the SFR and rent the condo2) Rent apartment, then search for a multi-family to buy and house hack3) Buy single family home and delay buying a rental due to save up for down paymentI would love to hear any advice or opinions on the options listed above (or any others) as well as, purchasing a property on a short time frame, and using a FHA loan on the second property instead of the first.

I'd prefer to use that as a downpayment to buy another whole investment property out of state.Based on those numbers (which also don't appear to include maintenance, vacancy, capex, property management) you'll be doing all of the work to flip a multi-unit property, and then keep it running with 4 tenants for <7% COCR?

If you are looking at a small multi-family of four units or less:Rent RollReview all leases, addendums, or other agreementsTenant payment historyAny violation notices, delinquenciesList of all maintenance in the past yearSchedule of capital improvements in the past 3-5 yearsUtility bill reviewP&L for current year plus the last 1-2Service contracts (landscaping, cleaning, snow removal, etc.)Inventory of all property owned by SellerThere may be more but this is a good start.

the other thing if its  a owner occ type loan there could be mortgage insurance.. and most banks sell their owner occ loans anyway.. now if your doing what @Levi T. talked about and going after commercial assets.. this was possible years back.my personal banker was in charge of their OREO and I got the list every week.. and bought a few subdivisioins from them they took back .. but this is small commercial bank where I knew the owners of the bank personally IE president and head credit officer.. and my banker is in charge of all the loan officers... and has banked me 24 years.. so yes its who you know.bigger multi billion dollar banks doing owner occ you can pretty much foregeta bout buying those in todays market.they want as stated to establish if they get a mortgage insurance claim and or they want to maximize profits.. there is simply not as much hangover inventory.. and or they will then sell off notes.. 

I am hoping to achieve scale through multi-family homes. 

Here are some options I'm considering:Rent out my condo, buy a duplex and live in one unit, rent out the other.Sell my condo, buy a larger multi unit like atriplex or quad, live in one unit, rent out the others.Rent out my condo, buy another 2 bedroom condo or townhouse, and rent out the spare bedroom through AirBnb.Please let me know your thoughts!

An example, our last major land deal was the entitlement and sale of land for a 453 unit apartment project on 16 acres to Lennar's Multi-Family Communities Investment arm last year.

FHA backed multi-family mortgages have outrageously good terms (85% LTV, 35 year fixed term, rock-bottom rates, non-recourse.)