For most loans especially for first time homebuyers, your lender wants to see a 2 year work history of the same job that you are or will be working (same thing if you are self-employed).

That's not really a full story so it's hard to say, but generally, if you don't feel secure or confident in the person you hired, you shouldn't have hired them.

Any advice for getting into Self-Storage as a new to CRE investor?

I am self-employed.

I plan to self-manage these properties and intend to operate my portfolio as a business, tracking all income and expenses while avoiding the commingling of personal and business funds.

I don't have any pending legal issues at the moment, but I've been thinking I should find a lawyer that I can go to for questions, to review documents, leases, etc so that I can have confidence that I'm not making any silly mistakes that will get me into trouble later on.

For someone who is self managing a portfolio of rentals, any recommendation for bookkeeping books?

In a matter of fact I can say pretty confidently that most SFR eventually would cash flow.

But there will be fewer of them, they’ll be paid for direct client service instead of self-promotion, and there will be many fewer big earners and low earners.

So we went into the commercial space and pivoted to self-storage.