You will be able to get answers to all of your questions regarding real estate investing, wholesaling, flipping, rentals, lending, self-directed IRA and Solo 401k investing, or tax and legal guidance from many of the knowledgeable members.

We are part of the group that charges a non-refundable damage waiver fee, i.e. we "self-insure".

I have taken a liking to Self Storage as an investment property and was hoping to get some recommendations on books for the basics when it comes to finding a good deal, properly insuring for any liabilities, mortgage loans etc. 

It sounds like you would almost be like a self managing landlord for these clients.  

Even if you self manage it and somehow get your expenses down to 35%, your still loosing -$83/month. 

Most basement guys I know are doing a job like that in 3-5 months depending on how far they take it and how many subs they use versus self performed work.

Profit from a flip is consider active, ordinary income subject to "all taxes" such as self employment taxes and reported on SchC. 

That is why I only look at deals that I can self-manage.I hope that helps. 

(I started my self-employed journey back in 1977 as a pool cleaner)

I don't feel ready, but I need to stop this self-limiting pattern.