Asking as I am in that situation right now, but I am probably evaluating that with a somewhat narrow lens of "where will I get most appreciation?"

Standard vinyl clapboard looking siding will peel off easily in high winds.

., and I believe I could easily get 1000 to 1200 mo. from my side after I move out. 

Worst case I bet you could easily  and with minimal cost, section off the basement into storage units for your tenants as an add-on to their rent.

With your net worth (and likely income), you can easily do passive and achieve a potentially attractive return profile as a limited partner.

Is it too hard to evaluate?

Properties that used to easily rent for $3k/mo won’t even get any showings at $2,200

Putting your money into stocks, especially $10k can easily drop to $7k tomorrow if there is a correction in the market and all you can do at that point is wait it out with no other benefits. 

Since it probably won't increase your income (rent), evaluate the cheapest long-term solution on the expense side.How often will you have to repaint it @ how much?

If you’re in a good market, you could easily be making an extra six figures with your license, just helping people in your sphere with their transactions.