I am looking to either buy a move in ready home or should I do find a fixer upper, in which both I would house hack.

The good news is that you might be able to find a fixer-upper that qualifies for 203k financing.

If a limb, from a neighbors tree, breaks off during a storm and damages your house, your home policy should cover it.

Duplex cash flow is negative because I am living in it. 2000 a month I get from the upper tenant.

When is the best time to buy fixer uppers??

I'm going to go out on a limb and say it's priced too high and that you should have listened to your REALTOR instead of trying to squeeze out an extra $9,000.If you don't trust your REALTOR, go find one you do trust and then listen to them.

I'm thinking of investing out of state, specifically in value add/fixer uppers.

And breaking even after six months to me sounds good.Are you always looking for more turn-key properties or will you do this strategy on fixer uppers as well?

I'd originally thought "A" was like the super hot downtown condos, upper arlington, etc..

Or you could look for a fixer upper and then use groundfloor or lima or other asset based lender to finance purchase and rehab and then refi with an asset based lender or flip and repeat and then have regular income to show in those other 6 months.