As a result, the Tax Court ultimately disallowed the deduction.The lesson here is clear: when attempting to write off assets such as RVs, boats, cars, or planes, meticulous record-keeping is essential.

Assuming a building footprint of up to 5000 sq ft, use could not support the need for a lot of parking (probably <20 spaces).Not interested in auto maintenance and other uses that require disposal (and potential runoff/dumping) of large volume of hazardous materials.Long term, I'd prefer something that contributes to the improvement of this area (e.g. a used car lot might be OK for a couple of years just to generate income, but I'd want to find something more beneficial after that).

Cost segregated property is not automatic. 

If I was just getting started I would purchase a single family home with a 2 car garage or large lot, build myself a new ADU and rent the main house to offset my living costs.

- set them up on automatic payments with an online rental property software.

Renting a house is like painting a car or house - 90% of the work is in the prep work.

- upping your max # of guests somehow- "no cleaning fee" & upping the nightly rate accordingly CAN be a big driver of bookings in some markets- having your listing/pics done professionally (by someone who specializes in STRs)- a great outdoor area- if you wanna spend $, i'm seeing lots of people adding pickle ball courts & more stuff to do outside like that - having a car there that they can rent on turo for cheaper than the rental cars from the airport

I have to do that when I rent a Turo car and it's just one more thing to deal with

It doesn't work that way for the vast majority of people.The average new car payment in america is $726, that's crazy to me. 

However, two things that are a big unknown and was wondering if this would automatically disqualify me... 1) I had a foreclosure on a condo that finalized in Feb 2019, so more than 5 years ago. 2) I work for myself and been doing this officially for 1 year only (prior to that I had a high W2 job).