Glad you are taking care of your home finances.

@Jonah Stevenson congrats on getting your RE license.Here's what we warn new investors about when looking for an "investor-friendly" agent:Be careful asking for investor-friendly agents!

I have a 2 unit property in the western suburbs that could be well suited to be an elder care home for 3-4 residents.

I only care about DOM.

should I pay a professional to do the work or do I attempt DIY?

I meant an experience with a financial professional. 

Take care of it now.2) If you want him to stay, doing so for free only works if your mother has money set aside to pay for everything (like investments or a large bank account), otherwise it is out of your pocket.

Accountants are in such demand, that the best are not even accepting clients half the time.The other problem I see often with accountants on here is that they specialize in larger investors, and have really high prices when you as a smaller investor do not need all the bells and whistles.Another thing I see is folks thinking they need to have a tax professional in their state.

I have met with sea wall contractors, done a full home inspection and met with another structural engineer and seawall professional that did an inspection and performed soil density tests around the property.

Internally, I don't care- please, please build a fence.