If your property is in section 8 housing, it would not be worth the time, effort, or cost to change over to a STR.

However I feel that I lack the knowledge to get started, if anyone has done this in my area I would love to hear your opinion if its profitable enough to be worth the time and trouble.

Is there anything that stands out as a red flag, or perhaps there are areas you think could be worth negotiating on?

The pool needs 7K worth of repair and 14K to demo. 

Like you said, they offer the 30k  worth upgrades or use it for financing.

The small extra investment of time/money in cleaning everything between stays (even swapping out a shower curtain for example) is worth the positive reviews/referrals you will receive from happy guests!

Hi @Bridges Young,There are several meetups in Charleston that are worth attending.

Honestly, I am getting tired of sending notices every month and the $50 late fee (capped in CT) is not worth it.

Once a year and when needed are also easy to maintain and remember as your policy will likely renew on a yearly basis. 

It could be worth checking in to and then you'll have some peace of mind that any and all damages would be covered.