I just don't see how the entry home buyer is going to be able to overcome this, this is just now another hurdle.

and so i'd argue that anyone looking to overcome challenges / criticism should have:-money-a planseems like OP has the former and is working on the latter =)

Not the lifelong SSDI for anxiety, mild diabetes, high blood pressure, etc. that a person can treat, overcome, and get a job.

You need to learn how to use all the tools available to you (financing, insurance, management, etc.) and to understand how they fit together in your toolbox, as none will give you everything (e.g, insurance is required and it will cover you for many situations, but not always; asset protection (LLC) is litigation insurance and complements regular insurance, by minimizing the target and making it unappealing).If you are a new investor, probably you will not have a lot of assets and/or equity to worry about (but even that is relative and subjective to each person tolerance to risk) so I would not worry about that till you pass that risk threshold (in my opinion 100K+ in equity, maybe 50K if you are really risk adverse) and you should be primarily concerned with finding good deals and growing your business first.

Can transfering the title to a land trust help overcome the owner occupancy requirement on JADU

Here are some insights from individuals who have embarked on this journey:Creative Financing: Many investors have used creative financing strategies to overcome the obstacle of limited capital.

You can "cure" a void tax sale with 3 years of adverse possession that starts on or after the date a tax deed could have been issued, In other words, you start with the date 3 years after the tax sale, and if some time after that the investor adversely possesses the land for 3 years, then the statute of limitations expires and the heirs cannot claim the tax sale was void.

For me, this was a huge feat I had been trying to overcome for so long, but little did I know what else was in store for me later on in my journey. 

Rent control and politics can be overcome.

Thanks Ken, found out someone in the neighborhood has designs on the property via an adverse possesion.