You already mentioned Mid term, which can be a great way to increase cash flow.

He does not mention any downside to reverting to an executory contract/ lease option/ land contract. 

Not to mention any damages to the property I will have to suffer as well.

I see you mentioned Hospitable.

As Andrew mentioned, you will have to be very price competitive to get January and February bookings.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Give it a few years and keep learning so when you can answer all the questions that real estate investors ask on here, you'll know you're ready.You mentioned your family. 

I should have mentioned that I have experience as a NJ hard money lender but I would be a newbie to Section 8 and OOS real estate investing in general. 

Now that is taken care of; time to address the renter's insurance.As mentioned by someone above, you can be listed on the policy as insured or interested party.  

I didn't mention it in the post, but I am forced to move because of military orders.