If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

I’m just concerned of legality of basement unit and like you mentioned permitted status.

She's not in great health herself, but seems like she can still carry on a few more years if nothing bad happens.

FL seems to have reigned in HOAs recently, so who knows what they are allowed to do.I know that in CA, an HOA can ban smoking in units because smoking is not a protected class and the HOA has an interest in the safety & health of the building. 

For example we pay our own income taxes, broker splits and all of our other expenses directly out of what we make including required E&O insurance, MLS dues, licensing fees, Board of Realtor dues, continuing education costs, marketing, advertising, office fees/rent, transaction coordinator/ assistant fees, health insurance, car insurance and maintenance, gas, tires, software, retirement fund, etc.We are not W2 employees with payroll taxes already taken out of our paychecks, company-paid health insurance and matching retirement account plus a guarantee of at least 40 hours paid work per week, sick pay, paid vacation… none of that.So if you’re thinking you’ll be able to pay an hourly wage typical of a W2 hourly employee like $50-85/hr… that’s definitely not going to work.

You looking for an attorney to sue yourself ( suing the hoa is suing yourself since you are a member of the community) may not be worth your time and you may be responsible if mold does grow while you have a tenant and then they complain of health issues since you have not addressed the problem.

@Ryan Duphorn  a  5 /2  and 1920 square feet IMHO isn't a good health care traveler accommodation unless you are in a area with a shortage of housing. 

I value my health and try to get 7-8 hours of sleep.

Consult a tax professional to optimize deductions and explore strategies like Real Estate Professional Status or short-term rental loopholes to apply depreciation to non-passive income.This post does not create a CPA-Client relationship.

Status quo and anyone born after 2008 will not be buying a home until they are in their 40's if they are lucky and we will have a generation of renters or kids whose parents passed down a lot of $ to them.Which one do you think will happen?