It includes a primary residence, as well as a detached garage/storage area in the backyard that I am looking to convert into an ADU (Accessory Dwelling Unit).

Investment Info:Small multi-family (2-4 units) buy & hold investment.

We are about to close on our first triplex and need some minor work done in one of the units. 

the nugget of gold in all this is the tax efficiency of Henry Clark !

., one unit of a duplex, top floor of SFH) will need to be a LTR for the co host?

I wouldn’t necessarily give up on your idea to add an accessory dwelling unit to your property.  

It does not.Here is the complete, relevant statute (as amended):"Real estate broker" means any individual or business entity, including a partnership, association, corporation, or limited liability company, who, for compensation or valuable consideration, (i) sells or offers for sale, buys or offers to buy, or negotiates the purchase or sale or exchange of real estate, including units or interest in condominiums, cooperative interest as defined in § 55.1-2100, or time-shares in a time-share program even though they may be deemed to be securities or (ii) leases or offers to lease, or rents or offers for rent, any real estate or the improvements thereon for others, or (iii) sells or offers to sell, buys or offers to buy, or negotiates or otherwise deals in real estate contracts, including assignable contracts, on two or more occasions in any 12-month period.The newest language (in italics) refers to individuals or entities who DEAL IN REAL ESTATE CONTRACTS. 

I feel this target can be achieved given recent cap rates sold in the area, and hundreds of thousands of dollars worth of renovations combined done by me the landlord (1 unit+exterior), and my amazing tenants who did gut renovations of their units.The general rule of thumb is to use 3 lenders for cash out refinance right?

Investment Info:Small multi-family (2-4 units) buy & hold investment in Waukegan.

If there was a demand from the city for "relocation fees", that sounds like they are saying the unit is not habitable and they are removing the tenant / terminating the lease.