I Wasted $240 on Both AI Subscriptions So You Don't Have To

Forget the marketing bullshit. Here's what these tools actually do in the real world.

Perplexity Pro: Google That Doesn't Suck

Every time you ask Perplexity something, it runs a live web search and tries to give you an answer with sources. Think Google, but instead of 10 blue links to SEO spam, you get one paragraph with the answer and links to where it came from.

What this means in practice: I asked "latest Kubernetes security issues September 2025" and got a summary with direct links to GitHub security advisories, CVE databases, and patch notes. No wading through vendor blog posts or outdated tutorials.

The 300 daily searches sounds like a lot until you hit it at 2pm on a research-heavy day. Then you're back to regular Google like a peasant.

File uploads work great - drop a PDF and ask questions about it. I've analyzed everything from security audit reports to academic papers. Way better than reading the whole damn thing.

The catch: It's useless for anything that doesn't need web search. Ask it to help debug code or write something creative and it'll just search for similar problems online instead of actually thinking about your specific issue.

ChatGPT Plus: Actually Good at Thinking

ChatGPT Plus doesn't search the web. It's just a really smart chatbot trained on data through 2023 (with some 2024 updates). But it's damn good at reasoning, coding, writing, and creative work.

Where it shines: Writing complex code, explaining technical concepts, drafting emails, brainstorming ideas. The new o1-preview model actually thinks through problems step by step instead of just word-vomiting the first response.

I used it to write a Terraform module for AWS infrastructure. It asked clarifying questions about my requirements, handled edge cases I hadn't thought of, and generated working code on the first try. That saved me 2 hours of Stack Overflow diving.

DALL-E 3 is solid for mockups and presentations when you need a quick image. Not replacing a real designer, but gets you from "ugly placeholder" to "decent enough for the meeting."

The massive downside: Knowledge cutoff means it's confidently wrong about anything recent. Asked about Next.js features from this August and it hallucinated capabilities that don't exist. Had to fact-check everything current with Google anyway.

The Real Decision

Look, here's the deal: If you're researching current shit all day, get Perplexity. If you're writing code or content, get ChatGPT. If you're like me and can expense both, do that. If you're already paying for Claude, Cursor, and three other AI tools, maybe you have a problem.

Pro tip nobody mentions: Perplexity's mobile app crashes more than a Windows 95 machine running Crysis. ChatGPT's conversation memory has the attention span of a goldfish - screenshot anything important.

That $20/month adds up to $480/year if you get both. Free tiers are garbage after you taste the premium features. Enterprise pricing is "call us" which means "prepare your wallet for surgery."

Still have questions? The FAQ section covers the specific issues you'll run into that the marketing pages never mention.

After 6 months of daily use, here's when each service will piss you off and when it'll save your ass.

Perplexity Pro: Great for Research, Terrible for Everything Else

When Perplexity Pro Works

I needed to find the latest Docker security vulnerabilities for a client presentation. Asked Perplexity "Docker CVEs September 2025" and got sourced results with direct links to the CVE database, GitHub security advisories, and recent patches. Done in 30 seconds.

Beat the shit out of Googling "Docker vulnerabilities" and wading through SEO spam, outdated blog posts, and vendor marketing. The source citations saved my ass when the client asked "where'd you get this?"

When Perplexity Pro Breaks Down

Asked it to help debug a React component. It kept trying to search the web for similar problems instead of just looking at the code I pasted. Wasted 10 minutes getting web results about unrelated React issues when I needed actual code help.

Bottom line: Use Perplexity when you need current information from the web. Don't use it for creative work, coding help, or anything that doesn't require real-time search.

ChatGPT Plus: Coding Beast, Knowledge Cutoff Hell

When ChatGPT Plus Kills It

Writing a complex Kubernetes manifest for multi-environment deployment. ChatGPT Plus with o1-preview actually reasoned through the requirements, asked clarifying questions about my setup, and generated working YAML that handled my edge cases.

Also saved my ass when I needed to write 10 different email templates for a product launch. DALL-E 3 generated decent mockup images when our designer was out sick.

When ChatGPT Plus Falls Apart

Asked about the latest Next.js features released in August. It confidently told me about features that don't exist and missed the actual breaking changes I needed to know about. Had to go Google it myself.

The knowledge cutoff is brutal when you're working with rapidly evolving tools. It'll write perfect code for 2023 patterns that are now deprecated.

The $240/Year Reality Check

Look, I'm paying for both because I'm a consultant and can expense it. If you're picking one:

Need current info? Get Perplexity Pro. Worth it just for avoiding SEO-poisoned Google results.

Need a coding/writing assistant? Get ChatGPT Plus. The o1 model actually helps with complex problems.

Already paying for 5 other AI tools? Maybe you have a subscription problem. Pick one and cancel something else.

What Actually Breaks

Perplexity Pro Issues I've Hit:

• Search fails with "Unable to search at this time" randomly - usually when I actually need it
• Citations sometimes link to paywalled content behind WSJ or Bloomberg paywalls
• GPT-4 model selection randomly stops working - shows "Coming soon" for days at a time
• Mobile app crashes when uploading PDFs bigger than a tweet
• Rate limit counter lies - shows plenty left but still blocks you

ChatGPT Plus Issues That Suck:

• Rate limiting with "You've reached the limit" hits when you're debugging complex code
• "Something went wrong" errors when you're on a deadline
• DALL-E fails with "I can't generate that image" for perfectly normal requests
• Conversation history randomly disappears - had a huge debugging session vanish
• o1-preview limit counter makes no sense - sometimes says 3/10, sometimes just shrugs

Both services go down during demos. Murphy's law of AI tools.

The Bottom Line After 6 Months

After spending $240 and countless hours with both tools, here's what actually matters: Pick based on your main problem, not the features list.

If you're constantly Googling stuff for work → Perplexity Pro saves time and sanity.

If you're writing code or content daily → ChatGPT Plus is worth every penny.

If you do both equally → You'll probably end up with both subscriptions like me, because the free tiers become painfully limiting once you're productive with the paid versions.

The real cost isn't $20/month - it's getting hooked on AI assistance and then paying for 5 different services because each one does something slightly better. That $240 doesn't include the other AI tools you'll inevitably sign up for. I'm now paying for Claude, Cursor, and GitHub Copilot too. It's a subscription addiction.

Want to try before committing? Both have decent free tiers. Use them for a week doing your actual work, not toy examples. You'll know which one clicks with your workflow.