I would guess 15-20% down payment would be required.

You do need to have everything that is charged for itemized and  send that letter showing deductions within the time frame required by your state.

You have an investing group, which I assume means an LLP of some kind which means you are paying the self employment taxes etc because you are not an individual.

I think they recently lowered the down payment requirements for owner-occupied multi fams.  

It seems like "most" lenders (at least the ones I've talked to) don't like the idea of rent-by-the room on a primary ... so they can't count my income on that particular property and they are requiring a 1 year lease on the whole house instead of multiple mid-term leases ... so essentially they want a long term lease.

Despite having obtained a permit from the HOA, it has been revealed that the proper procedure required obtaining a permit from the Florida State prior to seeking HOA approval. 

No seasoning will require that you did rehab.

I have funds totaling around 20k for a down payment (100k home), however for my planned strategy I’d like to target homes at max 200k which should require a 40k down payment.

That requires guidanceIf you are a lender, the worst loan you can make is in second position on an over leveraged Subject To for someone who has no money.

I am looking to expand and I want to purchase my first duplex to house hack or do my first flip which both ventures require me to have my financials in order.