1984 20 squares pitch is 2/12 composition shingles

You can likely hang a shingle and get tenants on your own.Do you own units in other areas as well or is this just for CS?

Recently resided with cedar shingles. 

Worn flapper or fill valve in toilet, replacing a faucet cartridge, replacing CH/A filters, change fluorescent ballast, adjust screen doors and windows, flush hot water tank, replace faulty breakers, replace a circulation fan in a refridgerator, replace agitator dogs in a washer, change heating element or ignitor in an electric or gas clothes dryer, lubricating a ceiling fan, replace a p trap under any sink, replace any wind blown shingles, change any thermocouple in a gas appliance, do simple 110v flux core welding, do pvc/copper/pex/galv. plumbing, etc.If you don't know how to do those things yourself, someone else is going to make money off of you.  

It's 1,000sq, asphalt shingle, not-complex.

The upstairs needs paint on all the walls, new flooring, a complete bathroom remodel, ceiling has some spots of water damage, a few windows need to be replaced, and an updated kitchen.The basement needs some waterproofing, framed-out rooms need drywall, mold needs to be cleaned (no gutters on the house and has been vacant for 2 years), spiral staircase needs replaced.The outside has asbestos shingling (I can put siding over it in my area) Roof needs to be replaced, and the yard needs a little work.

If your roof has 5 years or more life on it, get a new 4-point and wind mit - but please keep in mind that shingled roofs generally last 15 years on average if Florida (sun is a killer!).

Looking for a full roof replacement (asphalt shingles). 

the shingles will be so cold they will break when you hit them with a nail gun . 

Who should be going first,  the sider or roofer for the area where the shingles and siding butt up against each other on the second-floor roof landing.