(assessor, owner, another appraiser etc.) 

We would need to add the contingencies for title, appraisal, inspection, etc so just wanting to make sure to cover all the necessary items.  

I financed this deal with a hard/private money loan that was at 90% of purchase and no points, no appraisal, no fees, with a 14% interest rate.

If I make an offer which is contingent upon satisfactory appraisal and inspection, what happens if the appraisal value is lower than what I offered.?

I'm now refinancing the property and we expect the appraisal value to come in higher than the original ARV. 

The properties then appraise for $140K to $160K and she's pulling her money out with a new loan.

I bought my first home paying 20k over asking price with a 10k appraisal gap, but lucked out with a good interest rate (3.9%) this was in 2022. 

A few things to keep in mind when obtaining an FHA 203(k) loan:1) Improvements paid for with a 203(k) loan must generally be completed by a licensed contractor and are subject to approval by an FHA appraiser as well as oversight by the FHA-approved consultant if it’s the standard loan option.2) You must develop a remodeling plan, schedule, timeline and put it in phases. 

A person with a property in year 1 or 2 saying they have $400 a month in cash flow means they are missing a key metric in the information they are giving you unless the deal was100% financing and the only cost they paid out of pocket is the inspection cost, appraisal cost, and closing cost.

Go work for what you want, join a brokerage, get an appraisal license, get a real estate license, something.