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Do you think future employers would look down on a guy who payed for their flight time to get to 500tt for example?
Not necessarily. There are owners who have flown their own aircraft for a thousand hours before they decided to seek employment as a pilot. Is someone going to fault them for flying privately?
On the other hand, the experience one has is tempered by the nature of the experience. It's one thing to go buy flight time, but it's entirely a different thing to compete for a job, be chosen for that job, vetted, tested, trained, and to be proven in that job.
You may or may not find work at the 250 hour mark, and you may or may not continue flying while you're looking for work. I've known various individuals who bought a small experimental and flew the wings off it to gain some experience, while looking for work. I hired a guy once who dropped in flying his own Maule. It said a lot; he came to shake hands personally, and he was flying something that took a little bit of stick and rudder skill. I saw him fly. He did quite well, and went on to be the chief pilot at a regional before I lost contact with him.
Getting your CFI is not a necessity, but you'll find that most professional aviators, save those who came out of the military, have or had their CFI. I've let mine lapse twice, and regretted it. I had to go back get reinstatements, because later jobs wanted it. It's not wasted certification, and it's kept me flying at times when flying work was thin.
I had a furlough once in which I couldn't find flying work right away, but did find aircraft maintenance work. The same facility had some training to do, so I did that, then began doing some cargo work for them, and in short order I was staying flight current. It's easier to find flying work when you're flying, and that work lead to a good job flying, from which I was later recalled off my furlough. You never know.
You may not fancy yourself a stellar instructor, but then you may find you like it quite a bit. I did. Even if you don't actually go to work instructing, it does add to your perspective as a pilot, and it does enhance your resume. It's not wasted effort, time, or money.
I went to work as an ag pilot before I had an instrument rating, and I didn't start instructing until after I'd been flying commercially for some time. I know a number of pilots who didn't instruct, and many of them have gone back years later to get instructor certification for one reason or another. I know others who had it but let it lapse, and who regret having done so. For my two cents, get it and keep it maintained, even if just through refresher courses.