Most commercial lenders do not require any seasoning for that entity which means that you can create an LLC and use that entity to purchase the property immediately as long as you have the proper documents.

And with an HOA handling maintenance, have you checked their reserves?

Deposit rent into checking account, transfer excess funds into brokerage account, make money. 

Many avenues to help you do as much or farm out parts of the deal making that you are not proficient in.  

This is a great place to learn and to connect with people so take advantage of all the great resources.

Insurance proceeds are typically provided in a check that must be endorsed by both the policy holder and the mortgage holder. 

This is the case in a few states. 

When I check local real estate listing it’s evident that a number of these properties for sales are former airbnbs that were purchased in the last 2 years and clearly are not worth holding onto for the owners.

Get out and meet some other investors at meetups and that will help you curate what some of those ideas would be like in real life, with the input of others who have done it.

I would definitely reach out to several brokerages within the area that could better facilitate as the middleman when Insurance Companies do reach out.