STRs that I could use for personal use (family vacations) once or twice a year.  

Is there a website or service that helps create a welcome book to have rental information, instructions, etc?

Personally if it is a loser for 2 years, then it is a bad deal.

Downpayment was through personal savings from my 9 to 5 and remaining financing for purchase and rehab came from hard money lender (Easy Sreet Capital).

@Rhia MckissicMost states require a lease to identify the owner of a leased property, whether a person, trust, LLC, IRA, etc.Landlord = Lord of the Land = Owner per deedAgent = someone legally representing the ownerProperty Manager = Agent

You can find loads of online and in-person real estate events where you can meet many wholesalers!

But painting the exterior of a house for $500 is very reasonable, at least around here for any person of reasonable skill to paint a house.  

I personally specialize on the financing side of the house and help people get from where they are to where they want to be in regards to lending and financing these deals! 

Thanks so much, have already learned a lot from this site but looking to get more personalized advice. 

To OP: My personal research has shown little with regards to value beyond time.