Maybe AI can take over this industry to save everyone time and $ for buying and selling a house which isn’t that complicated of a process.

Yes, you may be making more complicated than it needs to be...

In my opinion things get more complicated if you try to invest from a distance when you are first starting out.

I would strongly recommend having a real estate-focused accountant look at your situation and prepare your taxes for you, as you are now treading into complicated waters where you can get yourself into trouble if your not careful!  

To be honest, on over 100 building permits last year in the City of Chicago, with many of them having some form of enclosed porch, I think only 2 were ever mentioned by the Department of Zoning where they brought it up as a "Concern" which led us on a wild goose chase of finding and sharing information, overally causing unnecessary delay to the permit review process and eventually coming to a close (some positive, some negative).

Why take unnecessary risk and kick the can 5 years down the road?

This is a complicated question because it depends on a few factors:1.

I have identified a property with significant value, but its purchase is complicated.

How do you recommend I go about this if you predict complications? 

While I don't have personal experience I think a rental car agreement would be a complicated thing to add to a lease.