Are people paying for extra flood insurance or other insurance?

I Enjoyed the extra viewpoint.

In reality he is a high paid, likely already working a ton, attorney - he very well may not want to average an extra 10 hours a week of work year round to make it work. 

If you want to buy your first property ASAP, house hacking (duplex, triplex, or renting extra rooms) is one of the best ways to start with a low down payment while learning property management.

I hate to pay extra money for a PI on work we have already done. 

(You say it’s worth about $100k more than you’re paying so figure an extra $15k.)Maybe you’d be better off partnering with the parents unless they have zero interest?

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.

While this is a great and highly motivating goal, most people are either clueless or incorrect in their belief as to what is required to obtain this “lifestyle”.Understanding of the “how to” get there is further obscured by the misleading, and often patently false “pathways” sold by real estate educational MARKETING companies as workshops, upsold to association memberships, upsold to mentorships.

If you don't intend to do that right away then do the 20% and save the extra cash flow.

Many investors do end up getting their own license because of this, others don't want the liability and extra work.