Quote from @Alex Silang: Stop playing around.

Having two people paying rent, but only one living in the house is not ideal unless both understand clearly they are liable. 

Ideally, the software can integrate with my google calendar. 

If you told him you have been playing pickup games for the past year and need help improving your jump shot, now he has evidence you're motivated and a specific goal he can quickly help you work towards.

You’ll learn way more hands on than spending money and another 6 months being led on by someone who is playing you.

I never had that come into effect on my single family home purchases since I never wanted to personally be on the hook for such a high mortgage, but I think it might come into play for an MFH. 

Reasoning for asking this is that it could potentially be a beneficial long play on acquiring a property through assumption, and as we go down in interest rates, utilize this monetary benefit to refi as it comes at a mere .5%.

South End’s growth should support that play.

Some of the best BRRRR deals I have seen play out this way:You buy a home cheap enough that when you do a renovation and pull out 75-80% LTV, your rent covers your mortgage and you have returned most of your investmentThis is for A-B class areas. 

I think the time of the year certainly plays a role.