When comparing comps, pay attention to additional features like private pools, garages versus carports, ADUs, or any other standout features often overlooked by newer investors.

Also, I have a pool and fireplace so I want to cover myself on the lease agreement.

Things like septic pumps burning out, steam room dying, guests catching the grill on fire and leaving burn marks on the hardi siding, emergency bug treatment, above ground pool which is ridiculously hard to manage in our heat & having no time to deal with it if it starts to go, laundry & drying time for all the towels and linens, etc, etc.There are plenty of things we can and will get better at, but I'm prioritizing the stress level of my people as well as the very near disasters we've narrowly avoided, over the little bit of extra revenue we'd generate.

Is it water front? 

I added a decent amount into the house (new paint, new hot water heater, brand new kitchen, better layout) but I’m not sure if that’s enough for me to appraise for 20% equity. 

We want to know exactly what interest rate we’ll pay on a mortgage, what the water bill will be, if the property next door is thinking of selling, and everything else that has even marginal relevance.  

The water bill can be transferred to the tenant's name.

When turning basements into ADUs, and the breaker box, furnace, and water heater are down there, what are best practices for handling them?

I love the idea of renovating your carriage house - does it have any water and electric hookups already?

New roof, new water heater, new Electrical panel, New HVAC, new Concrete driveway, new Concrete steps & walkout basement, Open space of kitchen and living room, fully finished basement with wet bar and new full bathroom, new windows.