Looking forward to hearing your perspectives on where you think this sector of real estate will end up.

It's not a good thing from your perspective to cross-collateralize the two properties, in the event that you ever had a financial problem.

Can I just send my tenant a Rental Lease Extension Agreement, or do I need to send them a fresh lease?

Not sure if that helps but perhaps gives a different perspective when thinking about where to invest.  

In my opinion, a big yard in the city is often not a good thing from a rental perspective because of litter and more yardwork.

Having a network of people you can lean into for knowledge and resources is a must in keeping yourself fresh, and it goes both ways, for sure.

From the buyers perspective, you want prorations based on rents due in contract as well as terms outlining any outstanding balance will stay with seller, but that buyer will make "best efforts" to collect. 

Does your perspective change if most of the lots have homes built on them? 

As a lender, my perspective has changed and I've covered costs and paid for title insurance for people I borrow from for my rentals.

Those are pretty standard operational expenses for a rental business from my perspective, but I'm not sure how the SBA would view them.