What tools or platforms do you find most effective for tracking payments and amortization schedules?

I'm glad to know I'm on the right track and that all the points you mentioned are top priorities for me.

It sounds like you’re on the right track with your cost segregation plan.

This will help you determine if you're on the right track or need to make adjustments. 

You only need a place to track tenant information, payment history, maintenance, etc.

You don't have to track your basis in the securities or calculate any capital gains.As always, please consult your tax professional for advice on your specific situation. 

Checklist: Here’s a quick checklist to get you started:Get a home inspection (optional but recommended)Fix any outstanding repairs or issuesCreate or customize your lease agreement (covering pool/fireplace)Set up tenant screening processesTake detailed photos of the propertySecure proper insurance (consider rental-specific policies)Establish a move-in/move-out inspection processClarify utility responsibilities in the leaseConsider a property manager if you prefer hands-off managementDon’t worry, you're on the right track by doing your due diligence.

The bigger the project the greater potential to get off track. 

Finding the true appreciation rate for specific towns can be a bit tricky, but you can start by looking at historical sales data, talking to local realtors, or even checking out some online tools that track market trends.If the condos you’re eyeing aren’t meeting the 2% rule, it might be worth reconsidering or at least getting a more detailed breakdown of potential long-term appreciation and other benefits, like tax advantages or rental demand growth in the area.

And do yourself a favor and join the VTSTR(Association), which tracks state and local STR regulations, which there are many.