PS Now would be the streaming service that the PS4 can use to play PS3 games, I assume.  Any potential issues with the service?

PS3 is cheap, wait till next year to get a PS4. Maybe black friday or some super U4 Bundle. Save money and play more games.

When I actually get the PS3/PS4 could be several months down the line.  Also, if PS Now shapes up to be good enough on the PS3-games front, then getting a PS4 might end up being the better deal (again, wont be getting it this month if I go for PS4)

Honestly that's all I'm saying. A special edition PS4 is on the way. I'll probably get mine when the Kingdom Hearts 3 special edition PS4 comes out.

Get a PS3. You got several years worth of games to play. You can get them brand new at a cheap price and they'll only get cheaper. You got many great PS1 and PS2 games available to buy on PSN. Besides, isn't PS Now kind of expensive? So I'd get a PS3. Enjoy years of gaming and then get a PS4 two or three years down the road when it's actually worth getting.

One of the benefits of owning a PS3 > PS4 is I don't believe you have to pay for Online gaming

I suppose it depends on the games you want to play, but I would say go with the PS3. It`s cheaper and has a huge library of games to choose from. The PS4 is still young, and needs time before it has a large library of games, but that`s just me.

I recently ordered some used Xbox 360's for $80 on ebay. They all work great and had 3 month warranties.

I just ordered a used PS3 from Gamestop for $120 (an extra $20 for 2 year warranty).

I don't know your financial situation, but I suggest buying used OR wait for Black Friday deals.

I think PS3 is going to appeal to you more given the type of games in your collection. But the 360 has a few notable JRPGs as well.

PS3. Even if by some chance these remasters did come out, you could still play the older versions for much cheaper on PS3.
I'd recommend: The Last of Us, Uncharted Trilogy, Red Dead Redemption, Skyrim, Grand Theft Auto V, Bioshock, Bioshock Infinite, Portal 2, God of War Trilogy, Metal Gear Solid 4, Mass Effect Trilogy, Assassin's Creed 2, Tomb Raider, Journey, Shadow of the Colossus HD, Metal Gear Solid 3 HD, Final Fantasy X HD, Okami HD.
Other than what I have listed:
Street Fighter 4 is a good fighting game.
Gran Turismo 6 is a good racing sim.
Ni No Kuni is a good jrpg.

So you don't have negative experiences with pre-owned systems?  If I get pre-owned, I probably will go straight for the PS3 if it's cheap enough.

My financial situation is relatively stable.  I have loans, but I can pay them (mine are lower than most) and have a net positive every month after all expenses.