I used dogmeat through about 80% of the game, but at some point I stopped using him because he dies to easily to tougher enemies. As for money, the only way someone can have a problem with money in fallout is due to lack of time.
Anyway, I made tons of money by exploiting the hell out of game mechanics. It involves absolutely no cheating or hacking. This is within game rules:
**spoilers to follow**
Basically this "exploit" revolves around respawning enemies at certain places in the game which are found by trial and error. An example would be "wheaton armory" and "fort bannister". One will constantly spawn raiders about once in every two days game time, the other will constantly spawn the talon faction guys along with one Mr Gutsy. Later on in the game, some of these places will sometimes even spawn a few enclave soldiers, and the raiders and talons will wield better more expencive armors and weapons.
By "farming" all these enemies over and over again, I easily got an endless supply of talon armors, weapons and ammo which I sold to various merchants all over the game. I stockpiled enormous amounts of loot in a locker in my house, then sold all this junk for big money. Eventually I was able to afford anything and everything in the game, and still had about 70k+hundreds of items and thousands of ammo. When merchants ran out of their money and couldn't pay me anymore because they were out of money, I exchanged my junk for their ammo or drugs.
What was really cool about this exploit to me, is that it was never "boring" to keep doing this over and over again. Every new fight was different and unique. I moved through the opposition with insane speeds because I was somehow able to recruit "Charon", "Star Paladin Cross" and Dogmeat all at the same time... I equipped them with power armor and some of the most damaging weapons I could find. Later on it was Fawkes+Star Paladin Cross, which was an even more devastating combo. Again, all this was done without any mods, cheats or hacks.
Also, because I chose the lawbringer perk, I got a constant supply of fingers from all these dead evil guys and sold them off for 100 caps each. Off course if I was evil this wouldn't be possible because good guys don't respawn as far as I know, and I'm not sure if the talons could be hostile to me have I been evil.