I agree with @Jonathan Greene here that the first step is thinking through what to do with the primary residence - you might try this tool that I built a few months ago to analyze whether you should keep or sell the primary residence! 

3) When was the property built and remodeled?

We also tried out REI Blackbook but not did not like it because was pretty clunky and hard to figure out.Now, being that we are not real estate specific, we have a general contracting business in Chicago; we have a pretty robust system built out in HubSpot, which we LOVE and definitely allows room for more growth!

I am not really a fan of the program because we have a very nice situation in our current home.Putting 20% down for a conventional loan is a steep task financially so I do not think that is an option plus I have been told by many of my friends with multiple MF homes to never use your own money to get into one.Then there is always using the equity we have built up in this current MF home we live in to purchase the next - I am not sure how that works but have done some research on home equity loans and believe that would be another option.Any advice would be greatly appreciated!

Apps built for long term rentals, like RentRedi, won't help you manage bookings from Airbnb and VRBO.

I also like the idea of using one of the units as a home base; this is smart planning and a good foundation to start with.In regard to Syracuse, you may have a leg up there as well since you live there with the Syracuse Land Bank.

I wish we had this mechanism up here in the NW It would allow many more projects to get built.

A 100k home in Podunk Oklahoma that was built in the 1930's, is going to probably need a whole lot more than 10% of rent going towards capex, and likewise a 1m home in San Francisco isn't going to need anywhere near 10% of rent for capex. 

These are all reasons to believe the neighborhoods that experienced the largest spike in new housing will effectively absorb the supply that was built in recent years.

I'm curious if these new tech can somehow help me streamline certain tasks or reduce dependency on scarce trades in your experience.Appreciate any additional thoughts I looked at 3d printing those machines are 800k plus.. and if you watch the video you need very large lots as you have to bring in truck loads of sand etc.. so thats not really going to work in an urban environment like Charleston SC were I have built 35 plus homes in the downtown core on lots that are from 12' wide to max of about 30' and roadways that are only 20' wide and have houses and cars on every lot expect the infill..