Each strategy has its own set of benefits and drawbacks, as well as potential returns and risks.Buying to Flip for Quick ProfitBenefits:Quick Returns: Flipping properties can potentially yield quick profits, especially in a hot real estate market.Minimal Holding Costs: Since the goal is to sell the property quickly, holding costs such as property taxes and maintenance expenses are minimized.Creative Freedom: Flippers have the freedom to renovate and design the property to maximize its resale value.Drawbacks:Market Volatility: Flipping is highly dependent on market conditions, and a downturn in the market can lead to reduced profits or even losses.Capital Intensive: Flipping often requires significant upfront capital for purchasing, renovating, and holding the property until it sells.Income Tax Implications: Profits from flipping are typically taxed as short-term capital gains, which may result in higher tax liabilities.Buying for Rental Income and Long-Term InvestmentAdvantages:Steady Cash Flow: Rental properties can provide a consistent stream of income through monthly rent payments.Appreciation Potential: Over time, rental properties have the potential to appreciate in value, providing long-term wealth accumulation.Tax Benefits: Rental property owners may benefit from tax deductions on mortgage interest, property taxes, and depreciation.Challenges:Tenant Management: Dealing with tenants, maintenance, and property management can be time-consuming and requires effective management skills.Market Risks: Rental income may be affected by market fluctuations and changes in rental demand.Liquidity: Unlike flipping, rental properties may not offer immediate liquidity, as selling a property can take time and incur transaction costs.Comparing Potential Returns and RisksBoth strategies offer the potential for attractive returns, but they come with different levels of risk.

Would this potentially trigger a tax reassessment on the property?

If these places are generating positive cash flow, what potential red flags should an investor be on the lookout for?

Additionally, expanding your search beyond Fairfax to nearby areas with more affordable options could enhance your chances of finding better cash flow potential.

Any deal with upside potential (expense reduction, renovations to drive revenue, undermanaged property, etc) the in-place cap rate may hold very little relevance to the deal.Per your follow-on question about generating higher returns: you are 100% right.  

Real estate has a lot more involved - loan paydown, potential tax advantages, time spent since it is quite a bit more "hands-on" than the stock market, repairs/maintenance etc.

Maxwell AFB’s presence in Montgomery is definitely an important factor, though keep in mind that just 12,500 people (out of roughly 386,000 people in metro Montgomery) work for the Air Force.As for the difference between the two cities, I’d say that there’s slightly higher appreciation potential in Birmingham.

You're definitely going to need a tax accountant, and RE attorney to help you out on this one.If your properties are under a company structure, maybe adding the children as partners to the company with some sort of dilution of shares tactic that can mitigate your potential inheritance problem. 

So when I speak to a potential client I do not pass them on to a team.

You need someone that clicks with you personally before engaging in a mentor/mentee relationship with the dedication and stress that may be involved.Where to find a mentorStart by looking within your existing network.