Reflecting on the entire experience, despite facing numerous hurdles, I feel a sense of pride.

There are numerous vacation demand drivers in the summer season.

In regards to finding cash flowing properties and improving your cash on cash return there are numerous posts and articles posted here on BiggerPockets about markets in the Mid-West that will provide these returns.Take some time and browse the articles and posts and you'll find what markets interest you and then you can start digging and doing your due diligence.

Choosing the Right Investments: With numerous investment strategies, property types, and investment options available, newcomers may find it challenging to identify the most suitable ones for their financial goals.

But numerous items you listed are a negative .....

There are numerous laws depending on the jurisdiction so I always suggest, if you can, go through a local attorney to make sure it’s drawn up correctly.

I've read a couple of bigger pocket books and listened to numerous podcasts and figured it's time to introduce myself! 

On commercial property would only be obtainable on class D property, i.e. property with numerous "undesirable" features.

This site is an incredible platform that has numerous resources so definitely take advantage of it all.

I also tried Stessa, which I liked at first because it's free, however the imports from my bank accounts were missing numerous transactions (their troubleshooting tips didn't work either).