It's all math. 

Looking for connections in the area related to all things real estate and property management.

In my state, we have to produce an itemized list of all expenses that came out of the deposit within 30 days of tenant moving out.  

File all receipts in a dedicated Google Drive folder.

For true private money lenders (not hard money), both parties naturally need to be protected but more so the lender since their money is at risk.

As a complete beginner with no experience at all, please guide me on everything I should know and all the steps I need to take to make a successful investment.Thank you in advance.

The county it’s in considers all leases under 6 months to be STRs and taxes them accordingly. 

Being someone who is interested and house flipping/ home renovation BUT is not handy at all, what are the best resources to learn and get better at this sort of stuff.

Asking for help is not necessarily one of my strong points, however I truly believe in the knowledge that exists within this forum, and I would highly value any and all mentorship that may be available to help get me going in the right direction. 

Maybe since you aren't allowing his family, they'll all pass....?