For starters, the absolutely dumpiest trailer trash studios/1BRs are about 800 at minimum. I've found a decent number of places that are $1,000/mo which would be pretty reasonable.
I would not recommend getting the absolute dumpiest place. The $1,000 budget to get something a little better is a good idea.
- Somewhere nearby - The concern here would if I increase my income enough to replace my job I might be locked into something that I don't want to stay with.
- Somewhere close to the fun and close enough to work - There are a few nice spots that are about 30 minutes from Philly and about 30 minutes from work, which is pretty reasonable. The problem is that it's not close enough to the fun stuff that it wouldn't still be very expensive to uber out there.
- Somewhere close to the fun - Philly has some places that are within that $1,000/mo range, but almost all of them are very small studio apartments. Which isn't a problem, I don't need much space, but my concern would then be the commute to work. The positive would be that I could basically walk to wherever I wanted to go on weekends and would save a ton of money on ubers. The downside is that Philly isn't exactly "nice" to walk around in later at night, and I'd have to get up quite a bit earlier to commute to work unless I'm given some remote privileges (which I doubt).
There are interesting choices.
I think #2 is the worst choice of all 3. You're not well situated in Option 2 to seduce Philadelphia women and you're also far from your workplace. You sacrifice convenience for nothing there.
Option 3 is a good option. You seem to know Philadelphia reasonably well. It wouldn't be difficult for you to do well in Philadelphia because you likely know Philadelphia's good bars and its good daygame spots. If I moved to Philadelphia today, it might take me 6 - 12 months to get a handle on that, though Google, Instagram, and other internet resources can help shorten that learning curve for transplanted adults. Walking later at night in Philadelphia isn't good as you describe. It's possible in Dallas in certain areas with good nightlife and good lighting but not recommended.
You are also good looking and that would help in Philadelphia, even if you don't have as many friends in Philadelphia as you do in Wilmington.
You could defend choosing #3.
I think Option #1 is your best choice. You stay close to work and close to your existing connections in Wilmington. While the 33 mile distance from Wilmington to Philadelphia isn't much, it is far enough that it's a separate scene. That is a similar distance as Dallas to Fort Worth. As a Dallas resident, I'm not regularly in Fort Worth.
You are doing well with getting laid in Wilmington. You know Wilmington's scene better than you know Philadelphia's scene. You get to keep doing everything you do in Wilmington and now you'll have your own space for sex.
The best thing about this is that you're an apartment renter with this choice. You can choose Option 1 and sign a lease for 9-12 months. If you're not happy with #1, you can choose a pad near the most fun stuff in Philadelphia then. Maybe you also change jobs too during the next 9-12 months.
