Not worth my time and piece of mind.

Good things take time. 

How did you handle tax prep when you first started investing, especially with a plan to scale over time?

I manage tons of homes for investors and owners, and I have this conversation all the time.

However, opponents argue that privatization could disrupt mortgage affordability, increase borrowing costs, and reduce accessibility to financing for first-time homebuyers and small-scale investors.How Privatization Could Impact Real Estate InvestorsIf Fannie Mae and Freddie Mac transition to private entities, several key changes could affect real estate investors, particularly those relying on conventional financing.

Really expedites the time it takes to reach FI when you can completely eliminate your housing payment and get into multis for such little down and start building equity/cash flow with each one.

Quote from @NA LudkeyLudkey: My spouse and I are looking to purchase our first investment property - a duplex.

If you do not, I would still love to connect sometime when time permits.

"I would need to get a cost segregation study done  in the first place" Need to get it done for what? 

Having one nearby so that you can manage it better means that you will spend more time cleaning and maintaining rather than hiring someone else to do it and thereby get host burnout in a few months time.