For the past month, I've been doing a short term rental for my 1 bedroom apartment in a 3 unit building. Now, I'm having trouble deciding if I should rent the other units short term vs long term. The other units are 3BD / 1BA and would typically rent for 2800-$3000/mo each, long term in my area. The building is located downtown of a touristy/beach town.

Here's some details about the numbers/location/property:

- $50-70k per unit estimated revenue for STR (majority is from 4 month peak season in summer/early fall). Three bedroom units.

- $36k long term rent not taking into consideration vacancies

- We will be doing cleaning/turning over units by ourselves. We don't mind the work, and already have a process/checklist down. We would otherwise be paying ~$20k/unit per year in cleaning fees.

- Downtown location, near restaurants and a 3 min walk to train station

- Only 2 off street parking spots, street is permit parking only but there is free parking down the street
- Units have just been completely renovated
- The city does not have any ordinances against short term rentals

The biggest hurdles for me are: we're about to go into a slump/down season; potential parking issues; and if one of the other units were rented long term - dealing with the hassles related to that. I worry about having bad guests throwing parties, especially with a 3 bedroom unit. It would also cost about $5k per unit to furnish it - this isn't that big of a deal but it is worth considering.

What would you do? Does it ever make sense to have long term and short term rentals in the same building? Does the difference in revenue justify doing it? Or am I just getting paid to do another job?

Side-question: anyone have cheaper alternatives to Proper insurance for MA? They're so expensive, but I'm having trouble finding an insurance provider for short term rentals.

Boston, Massachusetts

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Deciding on short term vs long term rental

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