This article doesn't hit your specific scenarios exactly, and may be a bit basic, but might help with some considerations-https://www.biggerpockets.com/renewsblog/5-SFRs-or...I'd say the biggest thing for your to focus on first is the numbers in each scenario.

Read more: http://www.housingwire.com/articles/39832-freddie-mac-renters-say-they-expect-to-stay-where-they-are

An excerpt from an article I read today for Nashville regarding the time-frame of the affect of the legislation:"The measure would immediately halt new permits for this type of short-term renting and eliminate existing permits over the next three years for this same type." 

There are actually 24 incorporated municipalities in Pinellas County, and each City/Town has its own rules and its own red tape.Here are couple of interesting articles on the subject specific to St Pete and surrounding cities:http://www.tampabay.com/news/business/tourism/st-p...In short: "renting a home for less than one month is illegal under city code.

http://www.commercialappeal.com/business/real-esta...I'm pretty sure the link isn't paywalled.  The main idea is that 1 in 3 renters in Memphis have to spend more than half their income on rent.As someone who is looki...

That CBRE article was a 2020 report, but based on 2018-19 numbers, which have little bearing on the market dynamics of a post-COVID world.

I recommend you read this article on OOS investing.

I also recommend you read this article I wrote for Bigger Pockets titled How to Invest in Real Estate Before Turning 21.

“Business equity line of credit: Use Real Estate as Equity” up to $500k, interest only. gather your business and personal tax returns, financial statements, articles of incorporation and other legal documents.”Vectra Bank - ColoVeritex, TexasHELOCWebster Bank, CTWAFD Bank.

@Steve StinsonBummer, I don’t have a subscription to WSJ, so I can’t read the article.