Best Paid Ai For Personal Projects + Instant Web Searching? (gpt, Claude, Perplexity, Gemini)

Hey everyone,

I’m looking to try a paid AI plan to help me manage several personal projects. I want to keep everything organized so I can easily switch between topics without the AI losing track of my background, forgetting important details, or mixing things up.

I’ll mainly be using it for:

Financial Planning: Long-term tracking, investment research, taxation, and exploring different scenarios.

Career and Business: Evaluating job opportunities, validating business ideas, and figuring out what best aligns with my goals.

Immigration: Researching relocation pathways, understanding application requirements, and keeping up with changing immigration policies.

One of my main priorities is real-time web research directly within the chat. Ideally, I want something similar to how Google’s AI Mode researches and synthesizes information, but with the ability to maintain much longer conversations and build on ongoing projects without constantly hitting usage limits or losing context.

I haven’t particularly enjoyed using Gemini for projects or long conversations because it often seems to refer back to the Gem’s context file rather than naturally building on previous discussions. However, I’m not sure if that’s a limitation of the free tier.

I’ve also heard great things about Claude, but I haven’t tried its paid plan for this purpose ,so I’m unsure how well it would suit my needs. Another important factor for me is that I want an AI that challenges my assumptions, points out flaws in my reasoning, and gives honest feedback rather than simply agreeing with everything I say.

Based on my preferences, between ChatGPT, Claude, Perplexity, and Gemini, or any other alternatives worth considering, which would you recommend for my use case?

Thanks in advance!