I'd really appreciate it because I'm very hopeful about wading into real estate in this region but I don't see how the math will work (even before factoring in my expected financing costs).

If I did my homework correct, Condos on a land lease just don’t appreciate as fast as others that are owned out right.

Maybe my math is off?

I'll do a bit of homework on the matter before I determine my next steps.

House hacking math tells us you'd be better off staying put if you are spending less than $1100 on rent currently.Now you need a new model to take into account the other bonus you get with your extra piece of land. 

If so, I would do a little homework on zillow, trulia, realtor, and see what studio's and one's are going for.

Now if they punch a hole in the wall . . .Heck, Portland is now including economic life in the calculations - Considering most or our City Commissioners have a hard time with HS math, this should be interesting.Most of your stuff looks like normal wear-and-tear.

Assuming your rate is accurate and it will save you $100 a month, do the math. 

I would do the math using a hypothetical 5% prime (4.75%) and test that against the total cost of the cash-out refi over a 3-4 year period. 

Most Landlords do a lot of homework preparing to be a Landlord, but tenants do little of the same prior to renting a property, so their expectations can be very unreasonable.