. - cash flow is difficult now with long term rentals even if you pick markets that have lower purchase prices than Boston.

Use tools like AirDNA or Mashvisor to provide market data on projected rental income and occupancy rates, and make sure your lender works with appraisers familiar with short-term rentals.

Plus with no state income tax, cheap insurance, and very low property taxes, I’m probably starting $20k ahead of most people, and that’s a tax free $20k.).

The Homeowners Insurance will include Builder's Risk.

That is unless you have a JV or other equity partner who is putting up the funds immediately with no lien, title insurance, etc.

Income approach Also known as the rental income approach, this method estimates the market value by analyzing the property's anticipated future income and converting it to a present value estimate.

I know I can get an insurance plan, but is it worth the headache?

. - Taxes are on the higher side at $6,000 yearMy Numbers: $115,000 putting 20% of my money $23,000 and finance the rest with total expense of $1,834Monthly expense numbers: Future Maintenance 13% $273 - Vacancy 5% $105 - Property Insurance 5% $105 - Property Taxes 23% $500 - Property management 10% $215 - Office/Travel/Legal 4% $84 - Mortgage 26% $552 - Monthly Cash Flow - $316 per month or $3,792 per year so Cash on Cash = 17%I think this looks like it is a deal worth doing and I also believe I can bump the total rent up by $50 each tenant which I think make it even better.

Based on my experience managing a significant number of rentals, leasing back to a seller can work, but it’s essential to approach it carefully.Lease Start Date:The lease should be signed at closing and start on the same day—Monday in your case.

Hello all,Has anyone sold a short term rental owned over a year  as a non real estate professional that qualified as short term capital gains tax deductions with expenses and depreciation?