Quote from @Jacopo Iasiello: Keep pushing forward, and may your journey in real estate investing be filled with success and fulfillment.Dear Jacopo, I wanted to extend my sincere appreciation for dedicating your valuable time to reviewing my forum.

First reassessment when closing under my name initially, and then second reassessment when transferring the title to a LLC , even though all happening within 30-60 days in the same year.Any advice would be appreciated.

Here are some pros and cons of each approach to help you decide:Paying Cash for One Home and Refinancing LaterPros:No Mortgage Payments: You won't have monthly mortgage payments initially, which can reduce financial stress.Equity: You own the home outright, giving you full equity which can be used for refinancing.Lower Costs: No interest payments and possibly lower closing costs compared to having a mortgage.Better Negotiation Power: Cash buyers often have more negotiating power and can close deals faster.Cons:Opportunity Cost: Your cash is tied up in one property, potentially limiting your ability to invest in other opportunities.Refinancing Risks: Future interest rates may be higher, making refinancing more expensive.Market Fluctuations: Property values might decrease, affecting the amount you can refinance.Buying Four Homes with 20% Down on EachPros:Diversification: Owning multiple properties diversifies your investment, reducing risk.Rental Income: Potential rental income from multiple properties can generate cash flow.Appreciation: You benefit from the appreciation of multiple properties.Leverage: Using mortgages allows you to leverage your investments, potentially increasing your return on investment.Cons:Higher Debt: You'll have multiple mortgage payments, increasing your debt and financial obligations.Management: Managing multiple properties can be more complex and time-consuming.Market Risks: Market downturns can affect all properties, amplifying risks.Cash Flow: If rental income is not enough to cover mortgage payments, you could face cash flow issues.Considerations:Financial Stability: Assess your current financial stability and ability to handle mortgage payments and potential vacancies.Market Conditions: Consider current and projected real estate market conditions and interest rates.Investment Goals: Align your decision with your long-term investment goals and risk tolerance.Professional Advice: Consult with a financial advisor or real estate professional to get personalized advice based on your specific situation.If you prioritize lower risk and less debt, paying cash for one home might be the better option.

I appreciate any thoughts and comments. 

If you think there’s good future appreciation potential, then that’s a reason to hold onto the property.

I will appreciate all the input I can get especially a reasonable person to do the logistics including zoning etc.

This makes sense as well and defiantly will learn from this information and I appreciate you taking the time to reply 

There are some areas that will never cash flow, rather where you will get a return on your money is through appreciation when you sell.

I'm going to connect with you so we keep in touch :)I appreciate the response.

It's a small pocket with lower supply, so if you can get a good deal, you'll likely see some strong appreciation.