For what it's worth, I tried to run your numbers using the proforma I use with my CFO clients and I'm getting an IRR (average annual return) of nearly 23% (see page 2): Kalamazoo Properties

A market like Boston has a long track record of appreciation in excess of inflation/cpi.  

Quote from @Omari Atkins: Is it worth it? 

I can't speak too much to the market on the Westside, but as far as affordability on the West Coast Spokane is worth looking into.

This requires a dedicated effort sourcing and analyzing hundreds of deals to find the one or two worth pursuing.  

In short, I’m trying to figure out if it’s worth pursuing an off-market seller financing deal versus getting a traditional loan and competing for the property on the open market.

In some areas with low water cost the expense of splitting may not be worth it.

Whatever you decide on your next investment, Little Rock is a strong contender worth considering.

Are there any house at that price point that would rent for $1200-1500/ month with 20k worth of updating?"

If it costs you thousands to refinance it needs to be worth it.