I don't want to allow a tenant/roommate to move into a porentially cold property with heater fix repair date/duration of repair unknown.

I would stay out of Wilmington ( city ) but as Eric said there are places in north Wilmington you could look around but may sit for an extended period of time.

Second I would love to extend my help to you.

@Troy Gandee Unfortunately I will be out of town for work, but thank you for extending the invite.

That increases income for the duration of the tenancy and creates a greater return with your annual rent increases.

The second mortgage would naturally be registered against title to protect the interests of your friend.If your friend extended you an interest-only second for 5-years (or however long until your primary mortgage term expires).  

Would the following be examples of typical downsides to this strategy: - rehab amount falls below minimum loan requirement - not being able to refinance / use deferred refi since I'm using a loan for the rehab vs. cash- ARV appraises less than expected, and hence presents a challenge in repaying the HML solely through a cash-out refi - extended holding costs through being unable to refinance until the required seasoning time period ends (e.g., 6 months, 1 year)Just trying to get an idea about what obstacles I should anticipate if using this strategy.

We had to extend the contract twice waiting on them.

We also implemented several property checks during the duration of the tenancy to ensure the property is being taken care of as agreed.So I would love to hear ideas both from commercial and residential landlords.  

They are typically more expensive than a conventional loan and shorter in duration.