I know this area is very popular and some say over-saturated (I think thats any popular tourist area these days).

Purchase price: $155,400 Cash invested: $40,000 Property is located in Cuyler-Brownsville an historic district within walking distance of popular Metropolitan District of Savannah GA.I purchased the property to get started in the real estate space, however I value the walkability of the property, its proximity to parks and nightlife.Although the area is a rated roughly as a “C class” neighborhood.

If so you can look into Cash Re-Fi (not as popular these days with high rates) OR look into Home Equity Loan / Home Equity Line of Credit.

Airdna has some great data - it's direct pull from Airbnb and VRBO + they post articles from time to time on market trends. 

I have read many books and articles on the subject, but I'd like to hear some perspectives from others who have already started their investment journey: when you thought you were all prepared and put your plans into action, what unexpected and/or difficult issue(s) came up?

Contrary to popular belief, this is not set because I believe it will give me a higher return.

Please see link below for reference.https://www.avail.co/education/articles/how-to-buy-or-sell-a... 

Some cities have embraced STRs, while others have stringent regulations or outright bans.San Diego, specifically neighborhoods like Mission Beach, Pacific Beach, and La Jolla, have been popular for STRs.

Not quite as big and doesn't have the outlets, but it does have Loon which is arguably the premier mountain in NH and some very popular hiking trails. 

Crowley also looks to be growing and coming into it's own as well the past couple years, though not at the same level of some other popular suburbs in the metroplex.