@Basit Siddiqi is exactly right that Philadelphia / NJ has some unique reporting headaches that are often screwed up, so whoever you work with, gauge their experience working in numerous jurisdictions, or their teams access to those subject matter experts.Those in the construction world and rental world open themselves up to some substantial opportunities from a tax planning perspective, but also need to be sure they thread the needle carefully on the real estate professional rules to actually qualify for them.

I could raise their rents to market and recoup the cost of the repair, but honestly, of the rentals I own, only two have AC.

Do you have all rental income coming in one LLC acocunt?

I'm curious, Is this PM out of touch with reality OR on how rental property owners, that don't self-manage, feels?

You got bad advice from your prior accountant.You received rental income and it should have been reported.it seems like maybe he was lazy and/or doesn't understand rental concepts.The only exception is if he is paying 'under-market' for rent in which case the property would be considered personal use.I would fix the issue and charge him market rent. 

Here's why:Future Cash Flow: Once your debt is paid off in three years, you’ll have a solid cash-flowing asset that can provide ongoing income.Asset Growth: Property values, especially near a university, tend to appreciate over time.Debt Reduction: You can leverage the rental income to pay off your debt, essentially using your investment to achieve financial freedom.However, personal comfort and risk tolerance play significant roles.

Here are a few:Invest in Rental Properties:Buy Rental Property Outright: Use a portion or all of your equity as a down payment to purchase one or more rental properties.

Find a good, quality, reliable handyman to help with repairs.Don't get into rental properties unless you want to get your hands dirty....

I am interested in adding a 264 sq feet space in my front yard, attached to the main home for rental purpose.

This code allows property owners to avoid paying capital gains taxes when they sell investment property and reinvest the proceeds into another investment property through a qualified intermediary, within a specific timeframe.For context, we support about a dozen luxury STR investors annually acquire Oregon Coastal vacation rentals with the majority of those clients originating from out of the area or State.