All,It is my understanding that I can not use a 10% second home loan and put it in an LLC to reap the tax benefits if I STR the property most of the time.

7) What tips or advice would you give to someone cold calling for the first time?

It would be wise to order a home inspection from someone who does duplexes.It would also be wise To order a sewer cam inspection.

What are the Best Practices in Planning a Tiny Homes Community?

I would generally try to avoid insurance claims if you can because insurance is getting out of control nationwide, and we are seeing in FL, TX and CA that claims can follow the house and/or you and make it very difficult to sell the home in the future.Within the mortgage expense category you have 4 separate charges: principal, interest, property taxes, insurance (if you escrow taxes and insurance which 95% of our clients do). 

We also own a single-family home with a detached garage and a separate lot that is currently secured with the mortgage of the single-family home (we've owned this for 10 months).

When house hacking, you need to allocate expenses and income based on the portion of your home used for rental purposes versus personal use.

We attempted to DSCR this property to pull out equity but were told by the lender (and two other lenders) that DSCR would not be possible given that the home is not appropriately zoned for how we are renting it.

no one drives buyers around anymore.. thats a thing of the way long ago past. they will drive to the home to open it up for the buyer..

Just to really drive the point home on how easy most of these owners are to find if you're using a true quality skip trace service, feel free to message me and I'll personally run a couple for you and send you full reports on the owners and possibly the owners' relatives if I see anything that makes me think you should be contacting relatives.