In my area it is a pretty simple process to split one lot into two and costs about $5000 total.

What other things should I consider to make things simple but also protect me from headaches.

I'd suggest hiring an attorney that specializes in property law and not tackling it yourself, but the process as a whole is quite simple.

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There is a simple remedy for this and that would be extending your inspection contingency.

Keep it simple like "Complete Kitchen Remodel", "Bathroom Remodel", "Paint Exterior or Interior", "Flooring Cost Installed", "Roof Replacement", etc...

It's good to remember simple day to day tips that will reduce maintenance costs down the road.

Once it is set up, it is very simple to categorize transactions as most of the things we do in this business are very repetitive.

I use cozy as well and found it simple for both  myself and my tenants to use. 

It might be a simple solution in the statute.