How long it takes to be financially ready is different for everyone.

If investing in that studio style, I’d highly recommend only the best asset qualities, i.e. walk-in with no stairs, good area, golf course or lake view, etc. 

You should also get homeowner's insurance to protect what is now your asset.

If I was your brother getting my REI portfolio started, is there any advice, strategies, links, literature, articles, or people to follow that you would recommend for someone extremely leery of financial risk?

Successful real estate investment begins with teaching yourself about the landscape, networking, initiating small, being financial literate, doing something, and never giving up.

I like the possibilities of creating through real estate through so many methods and allowance for financial freedom.

Get a financial planner not one of us on BP.

With my two decades in real estate, I've learned the importance of balancing potential gains with financial safety.

Long term I do see this property being a great asset so we don't want to sell necessarily.

You have to remember that book keeping is relatively easy, so it's not just the book keeping your are paying for; you are paying for a business advisor who will help you systematize financial processes, make strategic financial decisions, and take your business to the next level.