For example, the properties I held for many years have increased in value, have given me cash flow, tax write offs, etc. 

I have a hunch that you got some A I help in writing this!

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.

The revitalization in downtown Orlando could also drive future appreciation.

Also, if in the future I ever do need to redo the main line it'll be more expensive (L&M increases), I will have already likely spent thousand installing and maintaining the pump, and I'll have more tenants impacted by a sewer construction project (currently a 3 unit but will be a 5 unit at that time.)Help.  

As I've been telling more and more friends and colleagues about my REI journey, I've gotten more and more offers from these individuals to be money-partners in future deals.

Many investors do not account for the future and are often looking to put the least amount down.

When going into business regardless if it is RE or anything else it is wise to protect your personal assets. 

The 30-40k per year are written offers (not signed contract obviously but in writing nonetheless).

My goal is to continue to grow my wholesale business and start my own flips in the near future allowing me to grow my active income.