Or a roof and new HVAC is "small" but that is also $10-15k cost in my market. 

Here are the numbers:Location: San Fernando Valley (Los Angeles)2bd/1ba - 850sq ftRemaining balance: 314,000Zillow estimate: 676,400Redfin estimate: 713,749Rent Zestimate (Zillow): 2771 (I feel this is a tad high for such a small house)Cons of the house:Old roof mounted package unit, that eventually will need replacing (made in 1999)Still need to repair 4 sides of fencing repaired/replacedDriveway needs a slurry job1 hour drive from my current house with no trafficLawn needs a redesign (more drought tolerant stuff) - It gets very hot in the valleyPros:Mortgage is only 1760 all inPotential ~900 net/moI already have it...If I did sell it, I would like to buy something closer to where I live, but I also don't want to get dinged with any unnecessary taxes either. 

(ex. plumbing, a leaky roof, noisy neighbour).

Age of home and capital expenses to replace roof, a/c, pool equipment, how much does sand affect wear and tear(?)

New roof, flooring, windows, quartz countertops, and kitchen cabinets.

All the right things wrong with it ( needs flooring and paint vs bad foundation and roof damage). 

My husband is a contractor and owns his own roofing & siding business.

It’s got a new HVAC and roof, new exterior paint. 

So perhaps he'd advance you $5000 after you put on a new roof and then $10K after the rehab is complete. 

The leaves will soon be falling in Cleveland which can be a problem for your gutters potentially leading to ice dams on your roof, water in your basement or a variety of other issues.