For context — anybody who works in foreclosures — many sales are on HOA or COA liens. 

One thought is to reach out to the HOA and negotiate a community wide package contract with a single vendor for Home owners insurance.

If you own at Shores of Panama in Panama City Beach, I'd like to ask a few questions about HOA management and revenue in a typical season. 

An HOA lien?

Take into consideration the mortgage, taxes, insurance, HOA fees, and cash reserves for home repairs or replacements.

HOA fees if there's an HOA.

No STRs according to the HOA. looking at this from an investor/family man lens what pitfalls am I missing?

"for rent by owner", investors)-search for non-homestead properties in your county and send postcards to those owners that own homes that meet the criteria you want to focus on-network with real estate attorneys -network with trustees in banks that offer trustee services-look up court records of landlords who have filed their own evictions and send them postcards -network with HOAs that have non-homestead properties in that association -when you see a "for rent by owner" sign in your area, send the owner a letter -join Facebook groups (for rent by owner, landlords) and being to contribute -improve your SEO on your website-find someone who can help you gather landlord info from Zillow, etc. to name a few :) 

There is an HOA for the association for a total of 10 units.

These are NEVER restricted by eligibility of an STR license, some HOA's might have different rules.