If 2795 is the current market rent for a property like this, then you might raise it a little, so by 50-75 each year after the current lease ends to cover cost increases (prop taxes, prop insurance, labor costs, etc). 

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.

I personally believe that I am paying high fees to a syndicator for concentrated expertise in a specific market and niche.

Anyone thinking about home hacking will benefit greatly from your expertise on managing HOAs and how they affect various rental schemes.Ultimately, developing a plan that complements your lifestyle choices and financial objectives is the key to effective home hacking.

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. 

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?

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

Carrying cost loan (closing costs on loan and interest), utilities, etc can be written off from a tax standpoint to reduce your liability/