Less affluent areas that will benefit greatly from occupancy taxes and tourism may be a better bet.

Our plan in the near term would be to use the cash-flow to buy additional properties every 1-2 years, increasing cash-flow so that we can live off that income after 10-15 years.Given our modest goal of $10K/month, I am leaning towards Option 2 which is to use cash to buy properties and in a few years re-evaluate financing.Here is one of the new construction duplex properties I am vetting right now:Purchase price: $360K for a duplex.Expected rents: $3300 monthlyInsurance + taxes: $500Vacancy, Maintenance + Capex, Property Management (25%): $800Net cashflow: ~2K/month (CoC ~7%)

That might be something to consider, and we got a tax break as well.

Doing so will provide liability protection and shield your personal assets from potential lawsuits or claims related to the property. 

The only concern if doing quitclaim will trigger home reassessment, that will push property tax higher.Comments and suggestions are welcome. 

It can be used as income the year after you collect if filed on tax returns and offers deductions as well to offset monies owed. 

Investments in Opportunity Zones can offer great tax benefits, but when combined with a cost segregation study, the benefits can multiply.An Opportunity Zone are areas that struggle with poverty and lack the necessary access to economic opportunities.

Off the top of my head, I believe I'm paying them around 18% total commission (they charge 10% on all taxes, fees, cleaning etc).My question is - Should I relist my property now during dead season or wait until peak season?

Tax liens3.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.