Hopefully this helps clear up the main point of your post!

I'm considering investing in STR in Hawaii to diversify my investment portfolio (mainly for capital appreciation) as well as it being a regular vacation place for my family.

I have started investing for a few years and had some good results with a few GPs but even those GPs who had been coaching other people had really bad results this year (mainly no distribution).

Really the main challenge is going to be making sure that your wife understands what she needs to do to document her hours and activities.

Age isn't the main factor here.  

I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

Mainly because if I used that metric alone I would not have done my last 10 successful flips. 

In my experience, a successful BRRRR typically comes down to two main things: finding a good deal and managing an efficient renovation.

We also have a bank account at a smaller Chicago community bank, but there technology isn't as good to be honest.I think @Jonathan Greene's main point is don't step over dollars to pick up pennies. 

I think it comes down to two main questions:1.