Is it easy to regularly enter Thailand while renting a condo and traveling to other countries?

I have a very nice Condo in bkk, I can do a 1 year lease when do you think you will need it?

There are many variables as to how many entries are allowed, but it's guaranteed you'll eventually run into trouble. Elite or retirement visa.

I was doing the same thing, I lasted from August 2021 until March 2022 using 30+30 before I got rekt at BKK airport.

I did a month in Indonesia in October, a month in the UK in December for Christmas and 3 weeks in the Philippines in February. When I came back they were adamant it's impossible for a ~20 year old to be travelling like this without working in Thailand because at the airport they're only allowed 2 weeks for a holiday. Eventually they let me in after about 3 hours of back and forth conversation but I wouldn't try to use visa exempt again. For frequent leaving and re-entering the only viable option is the Elite Visa tbh, anything else you'll get pulled up on eventually

There is no limit on fly out/in per regulations, however it’s up to the IO at the airport on how they interpret it…apply for the new digital nomad visa or buy the elite visa

Much less hassle to use Airbnb.

It really depends on how much time you'll be in and out of Thailand. There's no written rule that says you can only enter Thailand so many times on visa exempt, or that you can only spend so much time in Thailand on a tourist entry.

But if you're not spending a decent amount of time outside of the country, you run the risk of eventually being questioned thoroughly by immigration when you are entering the country after a few times/months. A Tourist doesn't live in a country for most of the year, so immigration will say you're not using the correct visa or method of entry if they think you're trying to live in Thailand without a long term visa.