Will a short planned workation and job transition impact my DTV application?

Will my intended purpose in the cover letter cause issues?

Hey everyone, I'm planning to apply for the DTV. I'm a software engineer with a permanent job. I can work remotely from abroad (after coordinating with my manager and for a limited time). I plan to have my first trip for about 2 months.

I have two main questions:

1. ​Will a 2-month stay look okay for the DTV? I want this visa so I can legally do a short workation (and not via tourist visa) and avoid applying for tourist visas every year as I want to keep visiting Thailand every year (either as workation or just leisure). I’ve read here that some embassies downgrade applicants to a normal tourist visa. Will my initial short planned workation be an issue?

2. ​Will transitioning working arrangements cause trouble later? I plan to slowly transition from my permanent job to fully remote freelance work. Will changing employers or contracts down the road cause issues with re-entry, extensions, or immigration officers at the airport?

Appreciate any insights or experiences!

(posting anonymously because I don't want people from my company know that I'm leaving the company soon 😃)