For example, an uber driver might show they are making $3,000 per month but they might be spending $1,000 in gas and maintenance on the vehicle! 

Many times they thought about my concerns and even put them ahead of their own. 

Did you go ahead with converting to condo?  

That all being said, if you feel comfortable going ahead with it and and there aren't any superior leads then why not?

They consist of rentals, vehicles, & umbrella. 

If you want to allow them access to your Internet, go ahead.

If you have no track history I would park most in a high interest savings account or in a passive vehicle.

I’m currently adding 3 ADU’s in Santa Monica and spending $500k or so but rents from those units should bring in $10k monthly soo kind of a no brainer for me to go ahead and do.

My taxable for the business was only 16K though because I did a big sec 179 for a vehicle and did another set of big write offs for tax purposes.I also have had a roommate for nearly 2 years.

But a lease would prove that at the end of the tenancy you expected her to return the premises as rented and I would add a line in that says if the trailer is ever abandoned or if she fails to remove it on the last day of tenancy it shall be considered an abandoned vehicle subject to disposal by Landlord.Does your insurance company know its there?