Thankfully I was able to sell both houses and stop the bleeding.During the sale process I found out than one of my houses had a baseball sized whole in the roof and the other had two AC units that were not functioning along with mold that had to be remediated.

Will the roof need to be replaced within 5 years?

I recently paid someone to do my roof and replace the carpet (~5k expense) on my short term rental in 2023, however he won't fill out the 1099-NEC.

Licensed with permits ~$3,250.HWT standard gas single family low efficiency without exhaust retrofit $900.Sand and stain hardwood floors, natural stain $3 per sf.Paint interior walls, ceiling trim and doors 3 tone paint scheme 2 coats $3.20 per sf (floor area cost includes paint)Click lock LVT flooring install overlay inclusive of prep and quarter round $4.50 per sf (materials and labor)Asphalt roof installation 3/1 - 800 sf bungalow with 2 layers of shingles - ~$7,900Standard porch cap replacement with 2 new precast concrete steps ~$2,500Used stove or refrigerator delivery and install $350New stove or refrigerator delivery and install $HD model specificUse this as a general guideline. 

Your roofs might look good, but they might leak later.

Thus, I'd expect something like the following for the next three years for US rents: 1) 2025 will not see much national rent growth as we continue to deliver so much supply that prices remain largely flat.

It also kills two birds with one stone: an investment property, and a roof over your head. 

Have a small flat here that was just recently purchased and under mortgage.

The home needed a lot of work including roofing, windows, siding , kitchen, baths, and mechanicals.

I was told they flat out said no and the student was pissed.