Key points:
- Insiders buying stocks means they think the company will do well or the price is low.
- Ashford is a company that helps other companies in the hospitality industry with managing and advising their assets.
- The CEO of Kingsway Financial Services bought some shares of this company.

Summary:
This article talks about two companies where the bosses bought some of their own stocks. This usually means they believe the companies will make money or the price is good. One company, Ashford, helps other businesses in hotels and resorts with managing their things. The other company, Kingsway Financial Services, deals with financial services like insurance. Read from source...

1. The article is misleading by focusing on insider purchases as a sole indicator of confidence or bargain stocks. This ignores other factors such as the company's financial health, market conditions, competitors, and risks. It also implies that insiders have better information than the public, which may not be true in many cases.
2. The article does not provide any context for the recent trades or explain why they are significant. For example, it does not mention how the stock price has changed since the announcement of the reverse split and delisting strategy, or what this means for shareholders and investors. It also does not compare the insider purchases to previous trading activity or industry benchmarks.
3. The article lacks objectivity and balance by only presenting one side of the story. It does not consider any alternative perspectives or potential challenges facing the companies or their management. It also does not disclose any conflicts of interest or affiliations between the author and the mentioned parties.

There are several factors to consider when making an investment decision, such as the company's financial health, growth potential, market position, management quality, competitive advantage, and industry trends. Additionally, one should also assess the risks involved, such as market volatility, economic uncertainty, regulatory changes, geopolitical events, or specific company-related issues.

For the two stocks mentioned in the article - Ashford (AMEX:AINC) and Kingsway Financial Services - here are some key points to consider:

1. Ashford:
- The company recently announced a reverse stock split and delisting strategy, which could be seen as a positive sign of management's confidence in the future direction of the company, or as a negative sign of struggling to meet listing requirements.
- The company operates in the hospitality industry, which has been heavily affected by the COVID-19 pandemic, causing significant disruptions and uncertainties for the sector. However, the company also provides asset management and advisory services, which could be more resilient and attractive during times of crisis.
- The insider buying activity by the CEO and Chairman Monty J Bennett indicates a high level of confidence in the company's prospects or valuation, but it may not necessarily reflect the overall market sentiment or performance of the stock.
- The risks involved with investing in Ashford include the ongoing pandemic impact on the hospitality industry, potential delisting and liquidity issues, as well as management and governance concerns due to past controversies and lawsuits involving Monty J Bennett.

2. Kingsway Financial Services:
- The company is an insurance holding company that focuses on specialty liability and property insurance products. It operates in a niche market, which could offer some stability and diversification benefits for investors. However, it also faces the same challenges as other insurers, such as low interest rates, high catastrophe exposure, and increased competition.
- The president and CEO of Kingsway Financial Services, Larry J Swets Jr, has been buying shares of the company recently, indicating a positive view on the company's valuation or future performance. However, his purchases account for only a small fraction of his total holdings, which could suggest a more opportunistic approach rather than a long-term commitment to the stock.
- The risks involved with investing in Kingsway Financial Services include regulatory changes affecting the insurance industry, potential litigation or claims related to its products, as well as market volatility and economic uncertainty impacting the overall financial sector.