Also, running a flip with no money and hoping you get a good return with all the other stuff going on in the background starts to add stress, and you end up not enjoying it.

Now, with me being back I'm returning to my original plan of wanting to house hack in the Greater Boston Area.

This sounds like a solid return!

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

You'll end up with a dog that you can't unload at the end of the day when you've dumped thousands of dollars into it with no positive return. 

I agree with @John Warren I started in Chicago and expanded to Milwaukee cause the returns were better. 

The number of calls you make, are only important if you are guaranteed a specific dollar in return per call. 

Of course, with private lenders, you must give up equity or a return on the debt.I agree with @Jonathan Greene that the BRRRR market is difficult right now.

I've had low returns but in general all have made money.

Not what we are looking to do and all the MLS listings just don't pan out numbers wise so far.That's awesome that you got some returns on flips and found some buy & holds recently.