I don't want holding costs to go through the roof because of the weather, but I also don't want to limit marketing activities and purchasing properties to just the favorable weather months.In my experience it seems that there's a really interesting psychological component of how weather warps people's thoughts and plans.

Obviously this property is good cash flow right now, mechanical are solid and updated, roof is the worst will need repair within 2 years.

If an asset seems to be performing at NOI=5%, but 5% is a typical reasonable amount for a savings budget for capital expenses such as roof, siding, furnace, heater replacements or upgrades, etc. which means the more realistic truth is that your asset is performing at 0%. 

also know history on mechanicals roof, AC etc.  

If you’re going this route, make sure the PM company is under the same roof, the rehabs are quality and they aren’t selling to you above market (appraisal price).

I needed to work to be able to keep a roof over my head.

In my city there is a roofing company run by teachers.

The inspection report came back, and there are a ton of deficiencies( roof in bad shape, pier and beam findings suggesting movement of the property, improper electrical fittings, gas lines not to code, etc).

How are expenses paid for by the trust tax deducted, i.e. roof replacement, plumbing and electrical expenses, etc?

Look to see if the major things are in good condition, roof, appliances, HVAC, sewer lines, windows, flooring, etc.