I bought a house with a beat up ugly pool, too. Thankfully mine is in DFW - my sis had a pool in KC MO and prices for pool work there were a lot higher than here. So here are some thoughts from an ugly pool owner. The cracks in the deck can be worked with - my pool has a cantilever deck and there were NO expansion joints cut. When I had my pool remodel done, they cut in "clean" cuts where my deck had cracked and then added a few more so that it looked visually correct. So a "redo" on the deck might be nothing more than getting the expansion joints cut and new mastic in all your joints. If you wanted to paint or acid stain the cement, the smaller cracks could be patched and all of that gets hidden. And if you do it yourself you could rent one of those cool saws....Maybe not what you would do if you won the lottery, but if it bought you several years and saved you a few thousand, that would be great.
Whatever you do - PLEASE do not be tempted to paint the pool. Just leave it ugly for now. The sellers of my house were to have refinished the pool, instead they painted it. We almost didn't close on the house over it. It is a huge mess and cost me a lot more money in the long run as well as the huge mess of having to sand blast. We swam in our pool for the first year with ugly delaminating pitting plaster (with bright blue paint chipping off of it). Just be sure you are watching your filter because the pieces of plaster will end up in your filter medium and you are going to need to deal with that. I am sure there is a point where leaks and problems start to happen because the plaster is in such bad shape, but ours was pretty bad and I never had any of those problems - and funny thing, no one ever complained about having to swim in an ugly pool.
You may want to talk to the pool folks about your options on the tile. All mine (from around the same period as yours) was in good shape so we opted to keep it. I know the pool guy mentioned that he had just been at a big tile warehouse figuring out tile to go with some existing tile (the problem on the one he was working on was also in the spill over). If the tile around your pool is in good shape other than the stuff at the spa, you might be able to just replace the spa area with something that looks like it was intended to go in that area. May take a bit of work to get the right look, but holding on to our tile saved me about $1,500 (at a minimum - I was probably going to want an upgrade) - it would probably be more than that in your area. I just had my tile acid washed and skim coat of grout put on it to freshen the whole thing up - it is amazing what those two things can do for beat up old tile.
I would talk to the pool people and ask what you could do different to get the bid down. I ended up using a light that was about $1000 less than the one that was originally quoted to me. My concern was that the LED might not be bright enough and I would be stuck with a $1500 light and no way to back out of the deal, but in the end the $1000 to go conventional was a big price difference. You might talk to them about the difference with off season costs (some areas seem to be more giving during the slower periods). Also, I would sure call out several companies. I think most people here can attest to the fact that bids come in quite a bit different.
My pool got through the facelift a couple of months ago, and we love it. I don't regret trying to hold on to most of the older features (original kool deck, old tile, etc etc). Another thought is to act as your own general contractor. I wouldn't even consider doing it, but several people here have done so with great results. You will need to find out what the rules about permits are so that you can handle that. I found in DFW that there are only so many plaster companies, only so many pool deck folks, etc. If you can find them on your own you may save quite a bit of money. You could start by finding the pool tile warehouse in your area and asking them for a tile guy - the tile guy could probably recommend a plaster company, and so on.
Good luck!
