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

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! 

@Jesse Jones-Smithhi. i tend not to advise people on personal residence items because... it's too personal. so i'll just pick one thing you mentioned and provide a comment. 

I'll preface by saying I'm not a tax expert, but just went through a cost segregation as a REPS and this was my view.The benefit from pulling out these items coupled with the bonus depreciation far outweighs any incrementally higher taxes in later years, by quite a large margin. 

Having rental property is not what determines if you are going to take standard deduction or itemized deduction.

3) When was the property built and remodeled?

The address was submitted to their red book and now shows up online as official address when I try to ship items from Amazon or similar websites.

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!

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..