And if you lived out there and could self manage, maybe you're making 200/mo even.From a return standpoint, even at break even, you're gaining 8k a year in depreciation to offset against regular income so maybe 2k there. 

There are situations where we could have a paper loss but still be able to show some cash flow, which is ideal.One of the downsides to selling property 1 is the potential for depreciation recapture and capital gains from any appreciation.

Cash flowing and approximate gain of $80k in equity.

Instead of recognizing the gain of 600k - 100k, you get a stepped up basis at time of death.

BUT I gained tons of experience and was able to get in the game.Sounds like you won't find something cheaper than what you have going right now, but have you looked at the live-in flip strategy yet?

When we did that, they sent an invoice for the leasing fee of $999 for a tenant they haven't placed in the property.So end result is that we lost $999 with this property management company and a month and half without much traction to get our property rented.

And at some point the SEC will stand in the way from retirees and conservative investors, and others, from participating in the gains and wealth created by Bitcoin. 

I am wanting to move out of my current residence, and because of other benefits such as the experience I'd gain and the access to a low downpayment, all signs point to house hacking.

I'd try to buy and find something ugly and make the changes progressively before you leave, gain that equity, recast a bit, and in 4-5 years rent it out.

@Connor ChanterI'm not a CPA but based on your post as long as your mom is the owner of the house in Michigan she should qualify for the $500k capital gains exemption.