SC Coastal towns have gotten very strict with licensing, regulating, and permitting for STRs.

My two cents would be to start with a solid business plan that accounts for phased development.Also, even though you're outside city limits, keep an eye on county regulations.

The situation in VT with regulations is just terrible right now.

So all of the neighborhoods in Cleveland will have the same rules and regulations.

A home sitting for months might be because it was listed during a slower rental season.Marketing and Property Management: Some landlords don’t market their properties well, or they might have strict tenant requirements that reduce the pool of potential renters.3.

You're treading in RESPA-infested waters there and these are federal, not state regulations.Referral fees for ANY closing services on residential loans are strictly prohibited under RESPA regulations. 

As best you can find out the regulations and if possible the sentiment of the community. 

Hard money I view as more institutional and have strict term sheets that they follow. 

I can't tell from your post if your search is strictly based on listed properties. 

@Grant NashI have no experience in flipping/rehabbing and will attempt to analyze strictly on numbers.