Check out the BiggerPockets Podcast for a library of great information.

This is a very vast realm of business.

Check out your local library.

We are in vastly different markets but I really like your idea and think its a creative way to add an additional source of income. 

But when you're talking about a large family on Sec 8, the odds are very high that this is what you will get in there, no matter how good they looked on screening.But hey, don't listen to the vast majority of landlords of grade A/B and even C housing who would never, ever rent to Sec 8. 

Charleston is a great market from a vacation demand perspective, but the vast majority of operators are running STRs illegally. 

I know some basics from reading, but haven't seen much more in details here or in searches at my public library.

BiggerPockets has a whole library of books that are extremely helpful.Here are some of my favorite books in the BP Library:The Book on Tax Strategies for the Savvy Real Estate InvestorThe Book on Advanced Tax StrategiesThe House Hacking StrategyRental Property InvestingWhich of these 6 things have you reviewed recently?

I'm sure there are vast numbers of people that wanted to be RE Investors that "flamed" out on their first property and gave up, because of Tenant Issues, incorrect financing,being over-leveraged or any number of other horror situations people have gotten themselves into.   

But I would definitely check with your local laws and regs, every state, county and city can be vastly different with what is and is not allowed.