I know I’m going to make mistakes, but I would like to minimize those mistakes as much as possible by finding a mentor.

I assume this helps provide some filtering of those serious and those who aren't plus some minimal income that helps offset the assessment time involved also. 

I expect to use the income from flips to grow my landlord portfolio but I realize I am about to generate taxes at a new and frightening pace and want to make sure I minimize the liability as much as legally possible by being set up correctly and using the right accounting software that will allow me to track multiple flips at the same time and account for rental income.

Originally the plan was to get into an SFH or duplex and househack so I can minimize mortgage payments and start building some equity.However, with work being remote now I'm wondering what more experienced investors would advise in my particular situation.

Yes negative cash flow at the moment, but its minimal... 

I want to save money but I also want to buy something that will work well with minimal usage/operating headaches.

If your deposit is minimal you can factor that in to how risky this really would be.

Purchase price: $100,000 Cash invested: $35,000 Single Family 3/1 with minimal attic space, only about 1400 useable sq ft. - Building up on the back half of the house, adding a full 2nd story with 8' ceilings throughout. - Project has been delayed due to Covid19 and Architect and GC issues, but we now have permits, and have started demo.

I tried both methods and HELOC was much better because the cost involved was minimal.

It's cash flowing a bit but with a lot of upsides and minimal risk.