After years of not using it, for some of the reasons listed in this group and mainly because I didn't think it worked well in my market, I signed up for the 30 day trial that expires in 7 days.  

My main question is whether it makes more sense to go the seller financing route and pay off the principal in 8–10 years or stick with a standard 30-year loan.My thinking is that the tax deductions from a mortgage wouldn’t outweigh the potential equity I could gain over those 8–10 years.

Lenders stopped allowing rent by the room due to modifications done to the property resulting in functional obsolescence and significant cost to cure in the event there was a default and they needed to foreclose on the home and resell it, given that the main buyer pool for single-family homes are primary occupants. 

However, Opportunity Zone investments require careful structuring to ensure compliance.Evaluate your priorities: If starting a business is the main goal, proceeds from your primary residence (with the capital gains exclusion) might provide the simplest funding option.This post does not create a CPA-Client relationship.

I work mainly on the north side on Chicago and many realtors from south side call an area C that I would call a D and area I call B they would call A My grading goes like this.....

I plan on investing mainly for the hands-off nature of it.

I'm seeing house hack, buy a primary and rent out the ADU on AirBnb or the ultimate house hack, owner lives in the tiny ADU and AirBnb both levels of the main house in San Francisco. 

I've read BiggerPockets' Real Estate Investing book and am particularly interested in the house hacking strategy, as I'd like to move out of my current living situation.Our main dilemma is choosing between a single-family home (renting out one room to a close friend) or a multifamily property like a duplex or triplex.

Can you share what main use case that you propose to utilize our solutions would be?

Mainly for it's re-usability and flexibility.