The vehicle that you choose is going to come down to what you want out of life.

@Daniel Lozowy I Print handwriting on the envelopes only.If you choose to do a test then don’t send both to the same people.

You choose your skills and make your own schedule.

What made you choose Cleveland?

If you choose to utilize your wife as the cpa that a business decision for the two of you to agree upon. 

You can choose to do nothing at all. 

The other way to rationalize 100x rent or valuation less 8% (cost of sale) less an additional say x% (so as not to pay market price) is to look at other industries: if you buy a long term retirement plan and you choose to exit before the "break even" year (usually around the 8th), you pay a penalty.

Thanks @Marc BrennerFrom my understanding, a BRRRR is no different from a Flip, except one chooses to hold and rent, another chooses to sell?

I choose to live in my first property with my brother for 2 years to avoid capital gains tax.

Putting HVAC in any unconditioned space is a big no-no and should be avoided, if at all possible.No matter what you choose, make sure the contractor does a complete manual-J calculation (and ideally blower-door test) so that you know the system is properly sized.