I just got a 60 day despite my flights being 150 days apart. I simply explained I was going to do the 30 day extension and 2 border runs to Cambodia and they accepted it. So I think if you submitted your intention to convert to a retirement visa they may accept this. The only issue might be requiring 800k bank statement
unfortunately landlords aren't the ones who cop the actual fine even though immigration say it's the landlord's responsibility. It's a rule based to scam people if you ask me. If it was legit they'd send a fine to the landlord as apposed to taking money from the tenant and telling them to get reimbursed by the landlord