Sure, about one in 2000 times, by someone experienced enough to recognize a very unusual situation, having the capacity to act on it, having the financial strength, experience and tract record to be able to attract the needed capital, having the knowledge and ability to structure the deal, having the ability to manage and or reposition the property after purchase, and having the capacity to carry the negative cash flow until turning the property around or obtaining lower cost financing.  

We will self-manage from a distance.Thanks!

I own a couple Chicago MF that he did gut-rehabs on and his team still manages them for me.

Are you using a local property management company?

It is certainly more challenging to investing actively when you don't live in the market but if you have an investor friendly agent that has experience and connections to contractors, property management etc then it helps reduce that risk.

Another option you may not have considered is to work with a developer and build a multi-family property in a desirable area, leverage ECO construction benefits available ($5 to $15 per sq. ft.) and cost segregation and bring in a management company to manage the property once it is ready for occupancy.

Now new HOA management is issuing violations, saying No Commercial Vehicles allowed. 

After a few of those I felt comfortable enough to start investing in deals I sourced and managed. 

I've had a lot of success with Zillow Rental Manager in the past for quality tenants.

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.