Or actual help with setting up the 1031 exchange.I know Midland IRA or Exeter 1031, both can act as 1031 custodians (or whatever the proper term is).

Not sure the numbers are adding up (mortgage, taxes, insurance, closing costs) or that proper reserves are being allocated.

How do you properly gauge the work that goes into this? 

Check with Proper Insurance https://www.proper.insure/ they specialize in STR insurance

If the proper was listed on the MLS before hand most deff the building dept k ew its condition and has an idea of what was changed.

How do you properly read an inspection report?

@Ross Y.With everything you described in detail regarding your spouse already actively managing your rentals and being able to properly qualify as a RE Professional (included spending more than 750 hrs/yr$ in that role, yes, your Cost Segregation (including any first year bonus depreciation) can offset your other W2 taxable income.

The ADU/duplex idea is tantalizing (they could be 100k cheaper and yield higher rent than a legal technical duplex), but it's always illegal (when not owner occupied and properly licensed) and cities have a really big stick they can shake at you if your neighbors complain.

We will have 2 means of e-gress, proper ceiling height (7ft. 6in), 1,500 sq. ft per unit, etc. for the basement. 

The bridge is in rough shape and the engineering firm I had looked at it said that it would only support the weight of a pickup truck but would not support the weight of a cement truck or larger weights required for development or required by the fire marshal.