The plan is to use the proceeds from this rental to buy another rental property for about $650-700K, plus to pay off the home that they live in now ($260K owed).

Insurance being canceled due to the area and finding insurance for it.

The email was short and challenged us by implying we were looking for investing planning and not tax planning.

@John Brown Running a short-term rental (STR) on a subleased property, often called rental arbitrage, is feasible but requires careful planning.

While this can be good for long-term appreciation, it can also impact cash flow for buy-and-hold investors.Insurance Costs: Florida's hurricane risk can translate to higher insurance premiums for property owners.Competition: Florida's popularity attracts a lot of investors.

Hey Nithin, one of my client's closes today on a next gen home that they plan on renting out the separate unit.

Currently working with a mentor, and I plan to give him a chance before I jump to something else.

Start with the county, zoning, planning commissions etc.

Ofcourse I am planning to consult a lawyer first. 

I’m planning to relist the house around April when the market typically picks up.