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

Will the roof need to be replaced within 5 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.

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. 

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

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

Some investors think that just because they are section 8 they don’t care where they live, they just want a roof over their head.  

@Zach HowardAll 1800-2400sf, 3-5bd, 2-7 year old (when I bought them), stucco sided, tile roofed, SFR without lawns. 

A standard roof that use to cost $15,000 to replace, is now well over $30,000 to replace in many areas of the country.