Early on, I think people should be more conservative and establish a base (HYSA) and then regular (weekly or monthly) automated investments in low cost index funds. 

I've done several house-hacks personally with different strategies as well and have helped many clients do them in Pinellas/Hillsborough/Pasco/Manatee counties as well so if you have questions let me know and I can give you a rundown of your best options based on your preferences.If you don't want, or don't need to house-hack, then you have a couple options and that is going to depend on your goals, savings rate, and other details. 

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.

Mortgage remaining is around 85K and current value based on comps is right around 295k.

Looking back my whole plan was based on 5% mortgage rates.

I have searched for other places based on owners responses to guests. 

This is certainly text book and absolutely the proper way to analyze a deal.Im not sure what he owes on the home but based on the payment and the year it was bought and the fact that its 20 min from Austin im just going to throw out 500K for conversations sake.500K compounding annually at 3% for 5 years comes out to approx $578,000, and you have the loan paydown aspect as well obviously. 

This property is ideally located in northeast Colorado Springs with easy access to military bases, shopping, dining and entertainment.

Your dad's cost basis for the portion of the property he now owns outright (his life estate portion plus the remaindership portion he received back from your brother) would likely be based on the value of the property at the time it was originally transferred to both you and your brother.

You don't know what a good property is because you are basing it off metrics from a couple of years ago or the one percent rule.