@Paul Fogarty Yes, even if you overpay your total estimated taxes for the year, both the IRS and the California FTB may impose late payment penalties if any of your quarterly estimated payments (1040-ES for federal or 540-ES for California) are made after the scheduled due dates.

That still doesn't do anything about the imposing HOA, which I had not considered at time of purchase because my intention was never to hold, it was to flip, so I didn't do a cashflow analysis on it.

It wouldn't be fair for me to impose a management fee on those reservations.  

I received this response from Truvi when I asked them if they would be contacting/going after guests for reimbursement with these new plans...That said, our approach is always to avoid unnecessary guest involvement.

I’ve heard mixed reviews from owners: some say it’s an unnecessary expense, while others say it saves them time and stress.

You'll lose your primary residence homestead exemption (which caps property tax increases in Florida), likely pay higher mortgage interest rates or struggle to get financing (owner-occupied mortgages require you personally to own and occupy), and create unnecessary complexity for minimal liability protection when you're living there anyway.

A loan can work if she prefers structure, with IRS-required interest, but she could forgive parts each year under the annual exclusion.For a one-time $200K transfer, trusts or custodial accounts are usually unnecessary unless her estate is near the threshold.

They sometimes buy with a simple quit claim deed, and regard title insurance or paying for a professional search as an unnecessary expense.

On the flip side, HOAs can raise fees or impose rental restrictions, so it’s important to read the bylaws and look at their financials.

However, only two men were helpful (thank you to you both) while your first advice was sarcastic and unnecessary (who the heck would hire AI to rep them legally?)