I have yet to complete a walk-through of the property and see what renovations may be needed (potential for HVAC and interior, but from my understanding the roof and windows were replaced within the last 7-8 years).

The roof is over the next door properties property line.

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

Midnight leaking roofs, frozen pipes in the street all that.

No state income tax.3. property tax's some of the lowest in the country.4. quality of construction most homes are built with stucco and tile roofs and desert landscape compared to much of the mid west rust belt were its very common to be looking at houses that are 50 to 100 plus years old. and yards grow fast  snow sleet ice all take more wear and tear on your units.we do a lot in most of the mid west rust belt states. the prime motivation is price point and rent to price ratio for those aspects they are the best.

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.