There is nothing that ruins a business relationship quicker than poor communication and unexpected fees.Some PMs add a flat fee or a percentage on top of maintenance bills.

Here’s my takeThere’s obviously a big difference in “unexpected” expenses between a property in which just had a gut renovation including roof, all operating systems, siding, etc., and a older property that someone slapped a coat of paint on.  

I don't know if today's climate of the city recognizing a need for more housing might make some sort of small difference (something you'd have to discuss with them) but, other than that, this is an accident waiting to happen.

If you mix funds, then any lawyer for a plaintiff -- say someone who has an accident on your property -- can "pierce the veil" of the LLC and show that all your assets, not just that one property, should be up for grabs.Cheers.

Judicious use of leverage (debt) when the property will still cash flow positive after debt service; when there’s enough equity left in the property to refinance if advantageous, and when sufficient reserves are held to cover vacancies, recessions, and unexpected repairs5.

With this option, we're wondering if it's better to offer it as a 3 bed 1.5 bath with 2 bonus rooms (which we live out of), or rework one of the rooms into an actual bedroom to make it a 4 bed.With either option, we're also wondering if it's best to have the cashflow of our current house to offset any unexpected expenses, or if we should pay extra and try to pay off our current house as soon as possible.

I know of one scenario where an unrepped buyer missed closing by accident, so the seller sold to their backup and the unrepped buyer lost both the deal and their earnest money. 

(Fortunately, we were insured)Emergency Fund: Always have extra cash for unexpected events.Tenant Support: Keep good communication and support your tenants through tough times.Final ThoughtsThis July 4th was a disaster, but it’s also a stark reminder of the unpredictable nature of real estate investing.

So....... with my previous CPA (who has since unexpectedly retired) we did a cost segregation study on an asset that was placed into service in 2021 which broke down the bonus depreciable items into 3 buckets, a 15 year bucket, a 7 year bucket, a 5 year bucket and the rest would be on a 39 year straight line depreciation schedule as it is a short term rental.

Since you mentioned retirement its always good to be prepared for the "What if factor" meaning "If" something should happen or come along unexpected.