These are strategies used to use a loss to offset active income you might have from something like a W-2/1099 employment/contractor position for example.

@Oliver Martinez S8 Housing Commissions typically pay on time.Once a year maybe, someone makes a mistake and there are delays.

We are fully booked for high season (Dec-March) through 2026.I know this is not the typical investment, so totally appreciate any advice anyone may offer.

We typically assess the market activity before acquisition and my newer investors aim for properties that are already occupied.

Many have done similar  example  https://www.biggerpockets.com/forums/52/topics/999550-how-ma...

Everything is property specific in commercial, so you need at least one example property identified to have the conversation. 

However, my original question was not about standard expenses, but instead was about how to account for the planned upgrades for the property, beyond the typical maintenance.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

How does it compare with typical mortgages these days?