My advice as of the market right now is to hold and rent. With the market going upwards for sellers and rental rate staying pretty stable. I understand you do not like being a landlord and my suggestion would be to examine your lease and see how detailed and supportive of your goals it is. You may want to add a monthly inspection and if the house is not clean and kept up then you will be able to take action. Usually if you make your renters aware of what can damage them in a lease, they will respect and care for your property to the fullest. You could even extend your current tenant to a month to month after their lease is up if you are comfortable and happy with them. Watch the market and speak to an agent to obtain a CMA.
Those are my thoughts... sorry if they are drawn out.... more
The only issue I see is that you'll have to be able to qualify for the two mortgages. The lender doesn't care if you're upside down on the first house. They just want to make sure you're making your payments. You should talk to a lender or mortgage broker and see what you qualify for.... more