This took a lot of time.Stuff like cleaning the paint off every single outlet cover took forever, too. 

Humidity levels in basement is high at 64%A/C was 40 years of age, not functionalSigns of Ice damming on the garage sheathingFurnace is 19 years of age, unit didnot fire when turned on at the thermostatThe incoming 3-wire electrical systems is considered out of dateNo GFCI outlets anywhere (including in Garage)Walkway has cracking and settlementGarage floor, concrete has typical cracking and settlementBasement floor, has signs of cracking and settlementKnob and tube wiring in the home is considered obsolete and may pose an increased fire hazard.

When I wake up sleepless in the middle of the night I jump onto zillow, or dive into a podcast; When I get an unexpected break from work, I check out homes for sale; when I'm out and about, I talk to people about the homes they've purchased/sold; when I'm playing with or walking my dogs I have audiobooks playing in my ear.

Most states allow you to charge for reasonable vacancy and marketing costs associated with the unexpected turnover and any normal charges beyond wear and tear.

If it looks nice, but the boiler and hot water heater and anything else in the basement (electrical, plumbing) are old, you will still have unexpected cap ex on a "new" renovation.

Got a Home Outlet around where you reside? 

.- Repair subflooring, ceiling, walls holes, replace wall panels, door jambs, window sills, battens and trims, subflooring, electrical switches and outlet receptacles, etc.

The home has part of the outlets grounded and part of them not grounded and I believe it has aluminum wiring. 

If a large unexpected expense comes up he will likely struggle to manage the financial priorities.

Do I subcontract out all the individual skills or try to find a handyman that can accomplish a wider array of items (like outlets, lighting fixtures, exhaust fans, LVP flooring, etc.) and then hire subs for specialty items (roof, siding repair, painters, etc.)?