paid off house, not in llc what deductions can I take?

[Joesph Stark]

Hello,

Here is my situation that I've been having very difficult time finding a CPA who can help.

My wife and I have 2 houses, the one we moved from was my personal child hood home valued at $320k and has 0 mortgage. It is rented at $2500 a month, and is not in a LLC. (we have umbrella policy instead). Selling this home is not an option at the moment. We also do our own property management.

The previous home still has an open HELOC on the property with 0 balance as well, with a credit limit of $250K

We recently moved to a new home last month. 

My question is, what would be the best tax strategy to find deductions for our rental. Since the home Is paid off we don't have many deductions can take at the home.  

I apologize for the jumbled up thoughts, but here are the questions we have:

1. Would it be worth doing a cash out refinance on the first house to start planning to get our next rental? 
2. Would it make sense to withdraw from my HELOC and refinance the home into a fixed rate? Or should I just get a new cash out refinance rate? Not sure if that makes a difference or if it is worth while?
3. Deducting car milage is going to be very little benefit since our new home and our rental is in the same subdivision. However, would getting a lease vehicle for the purpose of our rental business be worth while and a 100% deduction? Can this still be possible if the home is not in an LLC?
4. Getting creative here: Would it make sense to Start an LLC, transfer the house and "Sell" one of our cars to the LLC, so we may deduct it as a business expense. I'm not sure what are the tax ramifications here if it is allowed or even makes financial sense?
5. Is it worth while putting the home into an LLC since it is paid off? Should we do the cash out refinance with the home in the LLC and with myself as the guarantor (since it would be a new LLC?) If the cash out refinance makes sense?
6. If we do a cash out refinance, should the funds go in a separate bank account, and can we use those funds to actively invest in the stock market?
7. Can we put aside some of the rental income into an solo retirement account (outside of our 401k/Roth IRA) and be considered a business deduction as well? If so do we need an LLC or S Corp established? Is it even worth while to do this?

Regards,

Jospeh