If there are many years left in the current term, and it wouldn't really impact the price if a tenant seemed to intend to extend down the road, the seller may be ok with you asking, and you can always request the ability to contact (not harass, contact) the tenant during due diligence.

If you need personal bank underwriting you are going to need income that supports debt-to-income ratios, and supports an expectation of income that extends into the future at least 3 years from now (time frame that lenders tell me). 

Nowadays, cash-flow in SA seems to mean that it covers expenses, without much cushion for the possibility of market fluctuations after an extended period of appreciation, or unforeseen expenses.

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.

Its reassuring to know that we have a community of people who care enough to look out for each other and realize that when one of us is hurt that we all suffer as a whole.  

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.