So that is always dependent on personal emotion.

Note that in most jurisdictions, if you rent the primary unit and live in the JADU, the primary now has become rent controlled. 

Only thing investors have to control is the cost of land. 

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

As a flipper, you are trying to control your costs to maximize your return on each deal.

If you are okay with someone painting over your original woodwork (even though the lease says they can't) or ruining your marble countertops when they dye their hair (true stories) then you may be emotionally hardened enough to rent your original home that you have lovingly designed.Consider, also that at times you will have to carry two large mortgage payments and decide if you are willing to do that.

The thing that scares me about condos is the lack of control over the HOA fees.

-he pays $550 of the $930 mortgage, and half of the utilities, which are not split, and are in my name. am I overreacting, or do I need to do some damage control on the tax front?

It is spring, and the tenants also mentioned the sump pump is also running some which is out of my control and should by considered in some of their living cost being that they are living on an acreage!

It might be worth exploring options for someone else to manage the rehab and for them to just manage the property once it is ready to be rented.Stay on top of things and don't let it get out of control.