My suggestion would be to get an investor friendly agent who knows a few local markets and have them guide you in the right direction.

@Katie Lyon Because our weather is more temperate over the winter months, we have much more consistency in demand across all times of the year, so typically the market stays fairly consistent through all seasons.

They can't keep claiming they don't have time to find a place to stay as they've had time. 

Can someone guide me / point me in resources on my options?

Consult with competent legal counsel to guide you regardless of your choice here.

I'm currently house hacking my multifamily in Danbury and have another duplex in Brookfield CT that could’ve been a house hack deal as well.My 2 cents are: Stay prepared (preapproved) and on top of the market because when the good opportunities come, you have to jump on it.

Maintain detailed records to substantiate deductions for materials, labor, and expenses, which can significantly reduce taxable income.While an S-Corp provides tax savings, it also requires payroll management and compliance with formalities, making it essential to stay organized or consult a tax professional for ongoing compliance.This post does not create a CPA-Client relationship.

If they insist on staying, then they abide by the contract, period.Tenants threaten to sue all the time.

We arranged closing during a slower period of time & had him leave everything (furniture, inventory, guides, etc.) literally bought it & could start taking booking the same day.

The longer it stays in the same taxpayer name before changing it, the better.I would also suggest you speak to your CPA before making any decisions.