After some thought, we figured we would offer to just buy it from him, with the idea in mind that we could supplement much of our mortgage with the detached guest house.After lots of conversations with a lender, I was pre-approved for the ~$300K the owner wants, and I was able to work out a Conventional loan with 5% down, owners pays 3% towards closing costs (he’s a good guy and agreed).

But, when you purchase an investment property with the goal of ultimately using the cashflow to supplement your own income, at which point do you stop saving up cash reserves in the bank (vacancy, disaster, capex, repairs, etc.) and start diverting the cashflow to yourself?

I'd advise also having a conversation with good insurance brokers that specialize in multi-units...so you get the right liability coverage there and perhaps supplement with an umbrella policy.

Then use the money from flipping to start to acquire rentals to supplement a stable income.

It seems a lot of these people are just using it to supplement the income they get from the normal operations of their ranches.

When a tenant’s rent is supplemented by a rental subsidy, rent means the total contract rent for the dwelling unit.

About two-thirds of respondents (64%) started side projects, while 53% sold valuables to supplement income.

SOTA can be accessed by households with recurring income from employment, Supplemental Security ...I TOOK OUT A LOAN OF TOTAL 80K I FEEL LIKE WHAT MY MORTGAGE BROKER IS ADVISING ME SOUNDS GOOD BUT A PART OF ME IS SAYING I SHOULD GO TO THE AUCTION TO FIND A MUILTI FAM..AND ADD VAULE MY SELFSOMETHING IS INSIDE OF ME KEEP ASKING ME IS THIS GUY TRYING TO TAKE ME FOR A RIDE BECAUSE HE KNOWS THIS MY 1ST TIME INVESTING IN REAL-ESTATE SO I COME HERE TO ASK THE BIGGER POCKET PEOPLE SHOULD I LISTEN TO MY MORTGAGE BROKER OF FOLLOW MY GUT?

I mostly want cash flow to supplement income with minimal distraction once the deal is done in order to grow my startup business (not real estate).

The areas you mention (and virtually all other retail RE in San Diego) are going to be initially cash flow negative implying you will need to supplement the expenses for a period of time.This does not mean that they are not good investments.