@Alejandro OrtizOut of state investing has its own risks and benefits but if you set up a good team (property manager, contractors, etc.) you mitigate the risks and reap the rewards.

Anyone have tips on how to put together some sort of packet to bring to him so that he knows this is a legit option and to help him see the benefits of this?

The AZREIA meetings are open to the public, but are a member benefit to being an annual member of AZREIA. 

For example, depending on your situation, you may not even benefit from various creative strategies.

I can't get the idea - how can we benefit from the fact that there are no more constructions in the city, if it is already oversaturated with supply?

Hopefully I can help a little.So, the way we think about your question is treating your HELOC payment more as a 'holding cost' that counts against your rehab budget, as more than likely, your HELOC balance should be re-payed back down to zero, once you achieve the rehab and cash out refinance / convert the stuff to the long term fixed rate financing.Part of the benefit of thinking of it this way, is that the HELOC payment is temporary while you use that revolving line of credit. 

House-hacking has many benefits that one can utilize, so you should definitely consider it!

For him to ask the question ‘but why’ to a $40/ month increase ( which is $1.33/ day... a cost of one of those beers he drinks) shows that he has no consideration of your financial responsibilities and/or no appreciation of the low rent benefits that you’ve been giving him.

This is a huge tax benefit.

Is there any benefit for letting the tenant reside there until we have a contract OR would you initiate termination ASAP to mitigate any potential marketing/sale conflicts with the tenant/tenant's family?