Who do you buy your insurance for your multiple rentals, personal home, vehicles and personal umbrella and rental's umbrella?

Two concrete entrances each.  24 foot wide since meeting County Road width requirement, decided on 40 Foot long, raked surface for traction, "Wings" on the front two sides so vehicles don't keep hitting corners of road, turning in to soon. 

Without REPS, those losses are usually trapped as passive.You invest in a Short-Term Rental (STR) and materially participate, making it non-passive even without REPS.Multifamily (2–4 units): Great for long-term cash flow and equity but offers limited W-2 tax relief unless REPS applies.Short-Term Rentals: Strongest W-2 offset opportunity if managed actively, though more operationally intensive.Commercial Real Estate: Larger depreciation and cost segregation benefits but still generally passive without REPS.Cost Segregation Studies: Can create large paper losses upfront, but those benefits are often suspended unless REPS or STR status unlocks them.A small multifamily is a great wealth-building vehicle and may help you shelter some rental income from taxes, but it won’t do much to reduce your W-2 burden unless you or your spouse can meet REPS requirements.

Also, what do the vehicles look like in the parking lot (Big SUV's, vehicles of the working poor, a lot of junk vehicles that don't run on blocks, etc...)

I have no knowledge of the principal or his investment vehicles.  

At 59, I now own only my second ever new vehicle.  

Moved those vehicles and put these in place.  

Keep an eye on the property condition, especially if you notice signs of occupancy like vehicles or fresh markings, as this could impact your ability to take possession after redemption.

Regardless there are many more tax benefits other than depreciation - mortgage interest, repair costs, mileage for your vehicle, home office deduction (and thus percentage of utilities/internet etc), home office products, materials for repairs, property management costs, property taxes etc.

A lot of new (and even seasoned) investors wrestle with the exact same balance you’re describing: invest where the numbers work vs. invest somewhere you also like/feel connected to.Here are a couple of thoughts that might help:Numbers first, emotions second – At the end of the day, the property is an investment vehicle.