Using property management tools like Buildingium, AppFolio, Cozy, TenantCloud, Stessa, Property Meld, and Fixed Repair helps run the place well.

You have to be prepared to sell yourself quickly or in detail.

a plan to refinance our current mortgage as well as get a HELOC.

Well,  for the past month I've been out bided on everything I bid on.

We fell in love with the island as a family and know it pretty well now.

It's more private, you don't need a do not disturb note on your door handle for someone not to bother you are 7:43 am on a Sunday.If you want to do well in STR now it's all about the amenities and experience.

Should I hire a contractor to add an additional meter that separates the ADU from the main house or charged another fixed amount for the main house as well.

@Jose Guillu if it's too good to be true...well, you know the rest.  

We don't do well with armchair quarterbacks.

I hate tiling as well...the worst is once you lay it out and are 90% done...grouting/cleaning SUCKS even more!