Can it be argued after having transferred tittle to an LLC all finances going foward weren't commingled and was operated entirely as a seperate entity.

LLC will increase your costs to operate as well as complicate your taxes and mortgage/financing.There is actually very little need for a LLC beyond physiological protection and for that reason you are probably better off not transferring at this point in time.

Other investors and lenders like to see overall performance first (overall gross and net profit, operating expense, annual return in percentage etc).

On the HUD website it says only that: At least 80 percent of the units must have at least one occupant who is 55 years of age or older; andThe facility or community must publish and adhere to policies and procedures that demonstrate the intent to operate as "55 or older" housing; andThe facility or community must comply with HUD's regulatory requirements for age verification of residentsThis all seems a bit too easy to me, but can't really find step-by-step directions anywhere to do this.

Money is made when you buy , not when you sell  Yeah I mean I guess this is true, but I suppose my confusion is how a property that hits every benchmark imaginable as laid out by members of this forum (1.1% rent of all in cost, <50% operating expense, 28% cash on cash return) could turn into such a burden on a simple refi?

Unfortunately there is no individual or specific governing body in regards to property management in NY State so there are a lot of illegal companies pretending to be property managers and there are serious consequences for operating as a property manager without being properly licensed in NY.

Besides your operating agreement needs this roles' breakdown anyway.

I want to get started the in the way I want to operate in the future, and I don't need more work to do anytime soon.

What are some of the roles that need to be divided in a partnership to try split the work load 50/50?

You and your wife could house hack, live in one unit and let the other tenants pay for your monthly mortgage and put some cash in your pocket.Even if you do choose to move away or renew your contract and PCS, you now have time to start finding a good property manager to handle the day to day operation of the property.