I think having the flexibility to choose what weekends my family or friends wants to come into town out weights the consideration of putting a tenant in there full time.I have researched a bunch of things that come into consideration before starting this and I would love thoughts!

Many investors from California are choosing to invest in the Midwest because of the low barrier to entry and yearly cash returns making more sense in these lower priced markets.

If the new builds are larger and you do not need to do any work, that would be the option I'd choose personally. 

Curious, why you are choosing the 2,500 deductible?

I have to choose whether to sell those units which will take them out of the rental supply.

I agree with you that it's hard to predict future liabilities in condos, but if you choose wisely (solid management, reliable developer, newer construction), you can reduce the risk. 

I'd recommend choosing a company that has a few years in business, but isn't too large.

Cleveland is great for section 8.NOTE - tenants choose where they want to live.

If you choose to self manage you are going to add even more work to your agenda. 

Did you ever choose a strategy and how is it working for you?