Very important to do your own research on all of these items and not just accept their projections as accurate. 

This year I just felt like it’s complicated to keep up with my invoices and give him itemized numbers.  

Other items: remove pine tree.

In terms of the math, let's look at return from rental income and return for equity:For each item, calculate a year's return, and there's your approximate ROIFor the ADU conversion: ($4000/month x 12 months)/$500,000 cost = $48,000/$500,000 = 9.6%That's before expenses, which will cut that number down by several points.

No side R or D will "win" from a regional banking crisis, it's a universal item to be addressed.

The secondary major real estate portals typically fall into the few minutes to a day or two to update - they're normally faster to pick up a new listing but can be slower to get updates to an existing listing.So - flat fee listings are typically limited service listings where the broker is just your onramp to get your listing into MLS and doesn't provide much beyond the required minimum after that - everything else is an upcharge/upsell - the one big ticket item I think every listing should have is a Supra lockbox just for security.

None of your items are that big of an issue for me.

I've only had a few maintenance items that have come up, but that goes along with owning rental real estate. 

Upon the sale of the condominium, the capital gains on Person C's sale would be calculated as follows:A. 33.33% of the sale price minus the original purchase price to account for the interest acquired via quit claim deed on July 7 2015.B. 16.66% of the sale price minus the stepped up fair market value on 11/17/2020 as capital gains for the 16.66% remainder interest acquired on 11/17/2020 from Person A.C. 50% of the sale price minus the stepped up fair market value on 01/17/2023 as capital gains for the 50% remainder interest acquired on 01/17/2023 from Person B.Total Capital gains would be the sum of items 3A, 3B and 3C above minus any allowed deductions, such as the home sale costs (closing, repairs and so on).As an individual owned rental property, upon sale the only way to avoid the capital gains would be to do a 1031 exchange and then hold the new property that is purchased for approximately 3 years before selling it. 

You should be able to charge for any of these items if you have receipts for the expenses.