New roof is a definite and I feel theres some issues going on in the basement...

Or is this lack of info worth being concerned about.The inspection is all that matters unless there are warranty items like the roof, HVAC etc.

I painted the entire house and laid out new roof.

My largest electric bill has been $12.00 Roof inspector did not do a great job this time.

Also of course I know it does mean holding back more money for repairs (two of everything, except for roof etc).

First thing to check would be for running toilets or leaks. 

Depending on your municipality. you'll need the realtor to let you in when you turn it on to look for leaks so you can tell the plumber to turn it off before flooding the property.

We're talking new roof, new electrical (wiring too, not just box), new AC, new kitchen with granite, stainless, porcelain at a diagonal, serious landscaping.

I priced out a roof replacement on an 8-unit building (4 upstairs, 4 downstairs) and I can get a new roof on an 8-unit apartment for the same cost as 3 SFHs.Scale is also a magic word along with Exit strategy. 

After the purchase, I spent 9.9K on a new roof and 1.3K on the AC system.