Owning one property with 100/month positive cash flow can be very draining if it is necessary to deal with tenant issues.

(this is not very likely because of your lack of experience and high LTV) This lender would be in a 2nd lien position and not very secure if you fail. 

Depends on various factors.But yes, if you have a rental property that is producing net passive income, you can invest on the property that has high appreciation potential but less cash flow.That way you can use the tax loss ( it might still have positive cash flow) to offset other passive income.This way, you can also tap into the equity of the appreciated house in few years and still enjoy the tax losses. 

Keep the cash flow positive, buy below market value and you should be in good shape, regardless of prices. 

My property has had a positive cashflow for years why should I have to keep it in my name for 6 months to put it right back into the same business it came from? 

Terms/rates/etc offered for first position mortgages aren't the same as 2nd.

The great thing about BP is you can go back in time and if memory serves me correctly this question has been asked before and people were a lot more positive.

The private money will be in 2nd position on a high LTV deal.

In my opinion it will calm down in the next 5-8 years, at that time I want to be in the best position possible to take full advantage of the market.

I knew I would want to re-position the property and pull equity out, so the penalty didn't make sense.