I guess I’m wondering where I should begin or what programs (FHA, NACA, Conventional, ect) people would suggest going with/looking into.

He specializes in getting it bought with cash (hard money) and then refi into conventional.

Jake,It sounds like the limiting factor on your file will be a combination of debt to income (dti) ratio and loan to value (ltv).There are many lenders out there but the majority of them have underwriting overlays that create more hurdles for borrowers to jump through.You and every other investor needs to work with a lender that only underwrites to Fannie Mae, Freddie Mac, and Ginnie Mae's base underwriting guidelines.All of that being said, for a conventional mortgage, Fannie and Freddie are currently limiting the maximum LTV to 80% for a cash out refinance on a single family home. 

That's conventional conforming Fannie Mae, not FHA, not anything else fancy.f) Know that once you are in escrow (seller has actually signed on the line which is dotted), the balance of power shifts much more towards the buyer. 

Your credit union has their specific guidelines that they choose to operate with and that is based on their appetite for risk.The base underwriting criteria for all conventional loans comes from Fannie Mae and Freddie Mac. 

.· Prepayment risk – Generally, the buyer in a conventional installment sale has the right to prepaythe obligation on the note.

For conventional loans with private investors, FNMA, FHLMC, guidelines are different.

If you ask seasoned investors about their regrets, most will say they should have started sooner.In other words don't overthink it, take advanatage of the low rates, find a lender who can do 5% down conventional and buy the best duplex you can afford: try to get one that is large in size, is in good condition and at a good location.

@Alexander Felice thanks for your response, I have 30 yr fixed conventional on my primary home , about 530 k left at 3.75% and looking for 30 yr fixed ,close to 3%(if I can get in near future ) as I am just about 30 months in current mortgage please suggest what is the optimal way in terms of fee and addition to principal lender put.also, what are the scenario when they don't need to get appraisal done ?

Also considering FHA vs conventional loans.