Working with a lender familiar with coliving setups is crucial.

It is the most popular software in the industry, and most Tax Preparers are familiar with it, which makes tax season easier.My Recommendation: Spreadsheets are usually fine for your first 1-3 properties. 3+ properties, you should use a software.

Besides Ben Mallah, what are some other resources that I can familiarize myself with to understand the current valuation and the trends? 

This can be far cheaper than having an in-house project manager to do this for you.Based off your statement "this will be my first time managing a renovation out of state", it looks like you are familiar with the renovation process.

If you're going to self-manage you should definitely pick market(s) that you are familiar with.

I own a complete real estate management company and am very familiar with the market. 

As for the owner portal, it works but I really haven't played with it too much from an owner's standpoint, so I'm not as familiar with what all it does and doesn't provide as I should be.

Multi-families offer more cash flow potential than single-family homes and are often easier to manage than a BRRR, giving you the chance to grow without the same level of involvement.Given your busy schedule and family responsibilities, a single-family or small multi-family might be a good start, letting you get familiar with property management while earning stable cash flow.

I am more familiar with single family residences so will likely start there.

Quote from @Gabriel Gutierrez:Are you familiar with Middlebury in Akron and, if so, your thoughts?