FHA vs Owner Occupied vs Traditional with co-signer

[Jennifer Horowitz]

I am currently out of work due to covid with no income, obviously cant get a traditional mortgage loan on my own. I hope to buy enough properties to generate enough income to never go back to my day job. However I am not sure which property type and which loan to get first. Im eligible for FHA and have great credit and capital, so looking at FHA (with a co-signer) as well as hard money lending, owner financing, and traditional mortgage co-sign options.

I am looking to buy 2 properties, one would be a two family that I could/would occupy to hack.  The other is a single family buy and hold which I am buying with three friends, we would rent it out and create cash flow on it while we own it.  

I need my first property purchase to generate "income" so for future properties I am able to get more traditional loans based off of that income.  Here is my conundrum in terms of strategy for the loans and what would benefit me in terms of getting loans, offsetting any capital gains taxes we might incur upon selling either of these properties etc:

1. Is it better to have my name on the mortgage for the single family with the other three women co-signers as my first property, use that income to prove out I have enough income to buy the 2-family on my own with an owner-occupied loan or regular mortgage?  

2. Should I buy the 2 family with a owner-occupied cosigned loan first and use that proven income to have my name on mortgage of the single family (as well as buy others I plan on buying on my own). 

Need help!  Thanks!

[Jennifer Horowitz]

@Michael K Gallagher the thing is, in after speaking to a bank and some other folks, the income i would get on the duplex would still have me at a negative debt to income ratio because id be paying the mortgage with that income.  So from my understanding I wouldnt get a mortgage to buy another property since it is seen as 0 income, that true?