Marker welcome to the forum, and sorry about the bad luck you've had.
Regarding your question about the oiling maybe this site will tell you if it is automatic or manual. From your description I cannot tell if you are talking about your right or left hand. There is a choke I believe on one of the handles. From this list you will see the vast quantities of models made by Homelite and the difficulty of being familiar with them all. If it is by the trigger or throttle handle on the left side of the handle, it most likely is the oiler button. Models that are automatic oilers have oiler buttons also, so it still may be automatic.
http://www.acresinternet.com/cscc.nsf/GasbyManufacturer?OpenView&Start=49.155&Count=30&Expand=49#49
Oregon the manufacturer of bars and chains for most saw manufacturers will send you a "Maintenance and Safety Manual" at their expense which will familiarize you will lots of unique things that are necessary for the operation of a chainsaw, sharpening which is frequent, tensioning of the chain etc. 503.653.4706,
www.oregonchain.com
To check if your chain is oiling, operate it above some old cardboard, it it sprays oil on the cardboard it may be automatic, depends how oily it is on installation. Oregon recommends soaking a chain in oil overnight before using for the first time, and if your saw has not been run it may be a consideration. The first link most likely will tell you if it is manual or an automatic oiler.
As a rule you fill your chain oil tank with fresh chainsaw oil at every fill of fuel mixture. Husqvarna another prominent saw manufacturer suggest rinsing out the chain oil reservoir with gas to clean it out ever so often. Because of the fact it has sat for a while it may be a consideration.
Chain sharpeners are sold where saws are sold, you only get a few sharpens with a file(so pick up a couple, come in diff. sizes for diff. size chain), and if the cutter is not in bad shape it only takes a couple of passes with the file. If you do not have the guide to make the file sharpen at the right angle the saw will not cut straight. The staff at the saw shop will explain it with the guide so you can understand better what I am attempting to explain.
They will check out your saw for a nominal fee, and explain the working also, if they are too busy selling saws to first timers, drop by (call ahead) a small engine service place and ask if they can show you, it will be money well spent. If you have a small engine you will need service sooner or later and it is a good way to meet the fellas.
Saws are noisy and damage hearing, some ear plugs or ear muffs are EXTREMELY wise, along with leather gloves and eye protection. Chaps are wise also.
Good luck in your difficult time.