This can provide a steady stream of income to supplement your W2 salary and build wealth over time. 

My husband and I are Teachers and Nurses but dream of supplementing our W2 jobs with passive/investment income. 

End goal is a bit different though since I am looking to supplement retirement income with cashflow which is 20-25 years out. 

The boss I was working for when  I read RDPD was a big factor in shifting my thinking from "supplement my retirement" to "get me the heck out of here!" 

HOAsThere are many HOAs that do not have wind coverage.

Maybe there's some semantic misunderstanding on one or both sides leading to all this confusion.I supplement my income with my public speaking.

The builder’s risk insurance can also provide coverage for lost rental income or loss because of business interruption.

These do require more time and organization though.Looking forward, after 5+ years of owning a property, assuming you bought in an appreciating area, you should have enough equity built up via tenants paying down your mortgage for you and appreciation to refinance out of the VA loan (if you haven't already) or even cashout to buy more or to supplement your earnings.Theoretically, if you have enough properties you could refinance at least one a year.

Florida did just have back to back hurricanes but a proper master insurance policy and coverage usually covers that type or perilYou are facing a declining cash flow situation which is due to the HOA fee's so while there is still a profit and you have equity sell and look for a 2-4 units.

Without this, it’s tough to calculate a realistic cash-on-cash return or DSCR (Debt Service Coverage Ratio).Condition of the Property: Are there any deferred maintenance or capital expenditures needed in the short term?