In your example I see nothing wrong and no red flags with this request.

RE transactions are extremely inefficient and that's red meat for big tech.

We have rough plans below (red outline is the original footprint). 

When the lenders pull out of a market segment it is a real red flag!

For example, often fire damage is water damage--they put the red stuff out with wet stuff.

But, if you keep up a pattern of switching farms every 8-15 months, my guess is that at some point you begin to raise red flags. 

Some companies clearly demonstrate red flags if you look on the reviews.

High Maintenance Costs: Escalating maintenance costs can erode your profit margins.Change in Neighborhood Dynamics: Shifts in the neighborhood that negatively affect your property’s value are a red flag.Better Investment Opportunities: Selling might be wise if you've identified a more lucrative investment opportunity.Cash Flow Necessities: If you need liquidity, selling a property can provide a significant cash inflow.Tax Implications: Sometimes, selling can be advantageous for tax reasons, especially if you can benefit from capital gains tax laws.Personal Financial Changes: Changes in your personal financial situation may necessitate liquidating assets.Retirement Planning: Selling investment properties can be part of transitioning into retirement.Portfolio Diversification: Selling might be necessary to avoid overconcentration in real estate.Legal or Regulatory Changes: New laws or regulations can impact the attractiveness of holding onto a property.Ownership Challenges: If the burden of ownership outweighs the benefits, it may be time to sell.Real Estate Market Trends: Anticipating a downturn in the market can be a reason to sell early.Interest Rates: Rising interest rates can reduce the pool of potential buyers and lower property values.Property Value Appreciation: If your property has appreciated significantly, taking profits might be smart.Lifestyle Changes: Sometimes, personal life changes dictate a shift in investment strategies.ConclusionDeciding to sell an investment property is a complex decision influenced by market conditions, personal circumstances, and future investment goals.

Well for only $200 more you could have bought her a Red Convertible Porsche 911.$120k to a school.$7k to an insurance outfit.Hopefully she gets more  benefit out of this major purchase than the many others who have not.Just my 2 cents.

It would definitely raise red flags if you did this multiple times.