Thank you for your insights and have a fantastic weekend.Hi Kevin - I’d like to hear from Long Islanders who have this experience as well.

I'd love to connect with people that are trying to do the same and with people that have already done it. i want to add value to the community  and be able to leanr from you! 

Feel free to reach out, I'd be happy to connect you to the network there and help you review anything. 

Due to distance, I'd be factoring in a property manager as well.

Vishal, I'd recommend you join some of the FB groups focusing on midterm rentals.

I recruited a couple of virtual assistants I'd met, whose skills complemented mine.

Bad idea, I'd follow the states guidelines on contractual agreements. there's always going to be vendors that your not pleased with.

In regards to listing with ALE Solutions there's also other insurance sites I'd recommend listing on such as Temporary Housing Directory

And although @Michael Plaks makes a great case about tenant destruction (he doesn't trust anyone :), if your model was a short-term rental you won't have nearly as much wear and tear I would imagine. 

But if you simply chose to schedule it this way - then I'd say no.