Nope - the OP appears to be a US citizen currently in Italy, so the very simplest way is to enter on a visa waiver (30 days), apply for a non-O visa at immigration (60 additional days), then apply to extend the time to stay for purposes of retirement, which gives an additional one year. I followed that process, and had my long term extension less than a month after we arrived."Have you researched the process for obtaining a retirement extension of a visa for Thailand? "
Visas are not extended, only your permission to stay is.
The OP would be best getting a Non-OA in his home country before coming to Thailand, as that will give him nearly 2 years here with just one border hop and the 90 day reports.
Inspiring to hear your life styling and enjoying your time in Thailand. We are undecided on Phuket or Pattaya, been to both many times , my wife is Thai and daughter Thai, are interested in a good intl high school that isn't so expensive , and me golf . how does where you are in north side of Pattaya compare to more south side?I think you will be surprised at how frequently family and friends come to visit, especially if they are from the northern climates! No better place to escape the snow and ice! We have never seen a temperature here that wasn't between 23 and 33 degrees C, so it is pleasant most of the time. Of course, we live on a high floor right on the shore, so we have constant sea breezes - haven't used AC in over 3 years - other locations away from the shore tend to be much warmers, and with very little air movement.
Downsides? There certainly are places where you don't want to go - i.e. walking on the beach promenade at 2 AM would be asking for trouble - but they are easily avoided. Most western foods are available but cost more (particularly imported wines), as in all of the countries we have lived, but Thai foods are incredibly cheap and delicious. Local wine s*cks, but the beers are fine.
Plenty of things to do. When we want to go out for a day, we head to Koh Larn island, just off the coast, and have a relaxing day at the beach with a nice lunch, or head down to Nong Nooch Botanical Gardens, an easy half hour drive. For a weekend, we go to Bangkok and explore the many sights, shops, restaurants, there. For longer trips, we have visited pretty much every city and island in Thailand, and been to Cambodia and Vietnam many times as well.
Have you researched the process for obtaining a retirement extension of a visa for Thailand? At first, it looks rather complicated but in reality, it is very simple and straightforward.