Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

This would also be where an appraisal would be ordered in a traditional sale, but if using a hard money Lender, they have probably already evaluated the value before offering you terms.5.

Back to my primary point--do your diligence and develop your own sense of conviction on the purpose of this venture. 

What is the best option for a landlord policy for someone who owns multiple rental properties(AZ and CA) and has no primary home or an auto? 

80% on primary and 75% on investment property I believe.

Income taxes- if needed can you use your 2 year primary residence deduction if a taxable event occurs.13.  1031-  if any part of the insurance claim is a taxable event is there some way to do a 1031 with lenient time frame adjustments?  

I’ve read in books of people getting past having to live in the property they own so they can rent all units year one of ownership(living on the property with an rv). Are there other more creative ways to start cash f...

So, winters are the traditional slow times for sales & rentals.

Maybe he's the exception.But the good news is - no matter what you do, if your brother just leaves it all as "passive" and doesn't mess with anything, whether short term rentals, or traditional rentals - the right tax planning could mean a box of his investment dollars that is effectively able to grow tax free. 

Going in, I have a HELOC that I can draw about 60k from my primary and then 25k in cash.