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.

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!

Most of the tenants choose to move-out given these two options, but at least the decision is theirs as opposed to them not having an option.

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

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

New investors actually represent a subset of our transactions and we choose to serve them because we find value in growing the overall industry.

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

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

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. 

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