The problem is that you're not allowed to do it intentionally.Also, I disagree with your attempts to plan for "after-Trump" taxation.

There are many benefits that plan can offer over a self-directed IRA, one of which being that you and your wife could possibly have 1 plan for both of your traditional and Roth funds.If you're not eligible for a Solo 401k, the IRA will likely become a better value proposition for you as your income (and taxation) grows.

.), Municipal Building (office of taxation), Office of Housing and Comunity Development and Office of Property Assessment per each office referral until they start referring me back to each other with no luck.

I'm a CPA and attorney with both a masters degree in taxation from a business school, and a masters of laws LL.M. degree in taxation and estate planning from Georgetown Law. 

The way to avoid it is to invest either via SEP or solo-401k which are excluded from such taxation. 

If I self manage my properties but want to take advantage of the LLC S Corp designation for single-tier taxation, can I pay my small business to manage my property so that I only pay business income tax and not FICA tax on the rent that I’m using to manage the property?

@Tomiko Graves An LLC is a legal entity, with no bearing on taxation.

Or is it more general - like quite literally you could take any property and transfer it from you to any arbitrary LLC and there would be no transfer tax (at the federal level)?

Geography, as you mentioned, and Taxation are another concern that should be addressed. 

Down side, there are two I am aware of that is you get taxed as an LLC and then as that income goes to you you have personal taxes (Known as double taxation), and the insurance and property taxes may be higher.