The roof is over the next door properties property line.

This usually means all updated electrical, plumbing, and roofing.

I've looked into roof stock as a possible option but I've heard nothing but negative reviews about them.   

In contrast, Fossum’s resume on Taxplanwealth.com ( Link ), details every aspect of his life including his girlfriend in kindergarten and everyplace he has worked in the last 30 years.

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.

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

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. 

And the other reason I wont accept small dollars or investors is you lose any personal interaction when you have 100s of investors and I like the personal aspect of this.