How can I understand the profitability of a deal like this, or is this just something that I'm not going to know until it all shakes out?

Be a people person and go out and shake hands, and talk to people in person.

Usually you want to paint other sections of the siding in a different color or install vinyl cedar shingle shake at the peaks with an accent color.

That roof will be expensive, assuming there are gaps between the roof boards under the shakes, you will also have to sheet the roof, I would guess you are looking at $10-15K to do that roof

I can't see the reason to go else where to make 1% or 2% greater return.. you would eat that up in travel costs alone.But anyway.. in my mind we are getting to a balance market.. and your correct rents are not keeping up with costs.. so will be interesting to see how it all shakes out in the years to come.I remember when I started in the business if you put 20% down or 25% down and the tenant just paid off your house  forget about cash flow that was a huge win..and why not.. its a forced savings safe investment tax benefits.. etc.. then it became you have to make money on your down payment this is what created that run..Maybe we will step back in time and break even will be great..

All the houses in the community have wood shake roofs and the HOA dictates that they just be replaced with Wood Shake.

You will need to be willing to visit the bank in person. come in and shake the banker hands etc. and take them for lunch too.

I'm always looking to meet motivated folks who are hustling to find good deals, offering new ways to fund projects, and anyone who wants to shake up the parts of the real estate industry that aren't working well.Best of luck and hope to connect.

I would sell sell sell and take the $500K exemption pay no taxes and stay in cash until this trade war shakes out. 

If anything, another market correction is going to shake more people into the rental markets, which will drive profits up.