Our pockets are not deep but we have full ownership of the land. 

But they are fairly deep scratches.

Markets generally slow during the fall/winter season.

Whether it's buying the first property, remodeling, renting, or selling it slows you down and eliminates impulse decisions. 

I did this in the MS market and while the advantages you pointed out were true.. markets that have slow appreciation and or areas where builders can keep building for low dollar amounts like the mid west.

He had specifically said he’s okay with the north fencing and knows its to keep the homeless campers out, and who the police are very slow to remove.

but generally - new accounting and property tracking softwares fall short in one of two places: 1) they don't actually generate financial statements that a CPA or Lender will approve, or 2) They can, but the learning curve is so steep or convoluted it's impossible for you to get help if/when you need it (I imagine this is why this thread is a little slow right now)Have you asked your accountant what they think will work best?

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

Take a deep breath! 

Start with solid research, make calculated moves, and take it slow—real estate is a long-term investment.Good luck!