That person already had that money spent in their head even before the property is sold

I have house hacked 2 single family homes in Colorado Springs, moved out with both rentals cash-flowing very modest amounts annually, and am actively looking for the next property around Allentown, PA.My 2 options: Add to my portfolio and House Hack for the 3rd timeI know that house hacking will be the easiest barrier to entry around a big down payment, has the chance for a lower APR with a primary residence loan, and I am comfortable using this strategy as I have done it twice in the last 3 years.

Obtaining a real estate salesperson license is relatively easy, thus the barrier to entry is nonexistent.

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).

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

@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

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.  

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.