Personally, I wouldn't use a heloc to then go purchase a primary residence, unless what you can rent the current SFH for enough to cover the current mortgage (assuming there is one on the property) and the heloc payments.

Personally I do not like providing appliances for tenants as the repairs and headaches start adding up.

When I had arrived I found out that this guy had one truck, his own personal vehicle that doubled as his work vehicle.. and some personal tools.

This is a good reference for myself and personal private lenders.

We have an LLC that holds real estate but have run into issues refinancing through the LLC when family is renting or ultimately living in the property so I’m also not sure if this should go through the LLC or be a personal purchase?

Hire a company/person that is solely a QI like @Dave Foster they do it every day and will keep you legal and on track. 

@Dan Groveyes, go to meetups (real estate or business) and meet people in person and build a networkbut... no offense... i don't think funding an entry fee in second position is a particularly compelling investment

No need for a PMS with only one.AirBNB and VRBO can handle things for you.In the end you won't save much time with only one STR.Plus, personal correspondence really works well to boost those 5 star ratings. 

For my personal education, which one insurance should I have?

If you want to go in person, just search in Stamford and you will find one.