We back into the "strike price", meaning the maximum price we're willing to pay for a property, by starting with a conservative ARV and then backing off our required profit, the rehab cost, the time value of money (carrying costs and interest), and a contingency reserve for unexpected expenses.

Equity paydown and modest appreciation would result in a small profit; not enough to justify a non passive investment but i will own a killer cabin.  

Fast forward three years: He’s moved out, and the property now nets him close to $1,200 a month in profit after expenses.

At the acquisition price points, and the market value of the units if you do decide to go wit a pm you’ll find yourself not being very profitable as most pm’s will charge $75 per unit min or 8-10% of gross rental income.

I worked them, remodeled them and made very little money and eventually sold them for little to no profit.

Am I being dumb by NOT waiting, because it’s unlikely - I assume - my next deal will be as profitable (I got very lucky on this one!)

You can make great profits flipping houses, but you can also lose a ton if you don't do it right.That said, I encourage you to be in touch with an investor friendly agent in Indy.

However as you correctly point out this is far more risky and or its risk capital compared to buying a income property.. but the reward can be strati-spherically higher .. not just a little bit but it can be life changing profits on some of these deals.

Give them a portion of the profits from the STRs and have a buy-out clause when you have the funds to refinance.I am sure there are many other potential options for you to look into, but just off the top of my head these 5 came to mind.

I found a killer deal, put 1k down as EMD and then wholesaled it for a nice profit.