Personally for me, leveling the house and turning it into a duplex sounds like a sweet idea. I would consult a local REA to find out what its potential appraisal will be when you do that. However, I would get a good lawyer to set up an airtight contract with the GC.
The idea of renting it out, I am not a fan of simply because you will not be able to cover the whole mortgage with the rent. The only time I would be ok with the rent covering only a partial amount of the mortgage is if I am house hacking. Just my 2 cents.
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