But in addition to that, I also connect my tenant buyers with lenders to help them get ready to exercise the option.

A particular strategy that may help you is to assume VA loans.  

People tend to waste a lot when everythings included, so this helps to avoid that problem.There are also companies out there that can install a meter in lieu of doing a full submeter to ascertain how much usage the unit is using monthly.

However will that help influence SFH or Luxury MFs in lets say the hill section to appreciate to the levels of 2k a month?

Hope that helps, and feel free to reach out if you want to dive into this more!

At that time we could renovate the ground floor apartment and potentially turn it into (2) apartments for a total of (5).My questions come down to how do we deal with the existing 40k mortgage, whether we can make it work so her parents aren't paying much in rent, if anything at all, and whether or not we set up any legal entity, like a trust to help the legal situation of paying off her sister down the road. 

What do you need help with?

(and I would definitely support paying the $149 for listing on FF)Beyond FF, Airbnb and ALE, it's going to take time and leg work, and which platform will depend on your market.

I'd imagine I have a referral code or something somewhere if that's helpful for you, might get you $ of your first box or something.

Networking with local investors through BiggerPockets, Facebook, and meetups can help you navigate the market, while avoiding common mistakes like underestimating expenses, poor tenant screening, and hiring the wrong property manager.Good luck!