This was a property that was under repair from the previous owners who realized they were in over their heads.

If you don't want to do that (which is very easy but most people just don't realize that) then you should look into a modern national.

Combined with a growing population, lower than average cost of living, inexpensive yet quality schools, a solid job market, and beautiful scenery nearby have made me realize the importance of considering various different aspects for future rental opportunities. 

I realize now I should have put my hourly rate in my lease up front... lessons learned I suppose.

Once you’re told to F off you’ll realize it wasn’t that bad, which will eliminate that fear you have and give you the confidence to offer on the next deal which can ultimately land you exactly what you’re looking for.

I realize this isn't exactly what you're asking for, but check out https://www.biggerpockets.com/member-blogs/6405/43427-what-the-heck-is-seo-anyway - it's much easier to build a solid SEO foundation into your website from the ground up than to re-do everything later on.

Once you realize it's not for you, you would go to Upwork, not Fiverr, and plug in Real Estate Investor VA and you can find a lot of good ones overseas for $5-$7/hour.

They very likely offer what you are looking for and just don't realize it because it's not one of their more common products. 

I love this but I also know I need to have cash flow coming in.In this process I’ve learned a lot and would like to advance my investments in multi family / commercial units.With that being said I realize I may not have enough capital for the projects but I read and hear so much about investors using creative financing to acquire these deals.What stories and transactions any of you have done with some creative financing to give somebody like me a better look into how can leverage a seller into selling me there property ?

In a Short term rental, any damage , and the few incidents have been very minor, is realized right away and paid for within a few days.