Go for it. You sound like you have some mechanical ability, more than you might give yourself credit for. For what you have in mind, you probably already have the basic hand tools, other than that hoist to help with the heavier stuff. 

If you do intend to do pistons and rings, sleeves? you will need a few additional items, but if your that far in it'll become a major overhaul and you would want to have your crank checked etc. At that point it might be best to let a machine shop help you along and do your block work anyway and then let you reassemble it at the point where things aren't so complicated that your not uncomfortable doing them (like putting your reconditioned head back on, carb, accessories etc.). 

Paint work isn't all that difficult either. Its all about prep and getting things clean. A inexpensive HVLP gun is what I recommend (I have a sears gun and a quality respirator - more on that if your doing paints with hardner, safety first) You don't have to spend big $$$ on Dupont systems etc. I've been very satisfied with the Agco paints. Use the right reducer for the conditions, take your time, make multiple coats (drying time between) and you 'll have a glossy finish. Everybody gets runs and sags. You just have to have a plan on how to deal with 'em.

There's plenty of people here to give advice, but mostly we'll be here to cheer you on. 

I've done a few myself, although not all have been Olivers. They've all been learning experiences. Some I still have, others I sold. You will be rewarded with the quality of the job you choose to do not to mention the savings in your pocket. I will also agree that I'd much rather invest in the tooling (that I would have indefinitely) than to spend that money to have something done I could do myself. It's an investment in your &quot;fun&quot; or hobby.