They will not be in a separate lot but a larger farmstead parcel.

I own my house but am looking to start with a separate property as first in my portfolio.

It has 2 separate dwellings.

it typically takes a few years just to recover the closing costs. those are the types of things that get sugarcoated / ignored and they shouldn't be.3 separate recent sources show that it is cheaper to rent than buy at high LTV in virtually every market.  

Hello, I have a two-unit SFH (first floor unit & second floor unit which share a main entrance but have separate private entrances once inside the house), located in California (I know...).

Also if I was cosigning I would have a separate agreement with this person to make sure I could easily take every asset they have in case this loan defaults. 

I would suggest to check with your local laws first.Most likely you will need permit ( I guess you can get away without, obviously not suggesting that :D)) but possible) , also check your zoning.If not possible to create separate unit legally, I suggest not putting an oven in the basement, and rent it without, or live in it yourself

It looks to be a separate login and payment, which is really disappointing.

Those funds should be held in a separate account.What specific responsibilities does the previous manager have to ensure a smooth handover?

Separate bank account, credit cards, signature blocks for every contract and document you are signing for LLC.