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

Appreciate that, Drago 🙏 Legacy and intention are at the heart of everything I do — real estate is just the vehicle.

@Cole Setzer, yeah and a helluva race driver back in the day

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.

Tail of the Dragon only appeals to real drivers, and it's often so crowded it's more like a senior citizen tour.

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

It’s a walkable event so no one will be moving their vehicles.

Can we combine the DST strategy with retirement vehicles (Solo 401k, SEP IRA, Traditional IRA) to shelter more of the proceeds, or are   those completely separate lanes?

The owner is in the driver’s seat.

Compared to mobile home parks, RV parks generally experience more wear and tear because of the constant movement of vehicles and guests.