For right now, I think you're better served handling that yourself and partnering with a CPA on the tax work. 

Plus, they handle all the day-to-day stuff like managing tenants and handling maintenance so you don’t have to worry about a thing.

Curious how someone with a bit of real estate experience would handle this type of situation.

If you do the deal, ensure you have your property taxes set aside, because with seller financing there is not an impound process to handle the taxes and insurance. 

I appreciate the breakdown there between how some might handle the relationship.

As of now, I can see tax planning being beneficial to handle 2 people filing as single because we have to figure out how deductions from the mortgage will work.

I handled our rental unit renovations, but they weren't huge and this seems an order of magnitude greater.  

Here are some key things to consider:Find a Sub-To Friendly Title Company or Attorney – Illinois is an attorney-close state, meaning real estate closings are typically handled by attorneys, not title companies.

Another great strategy is leveraging trained VAs to handle lead generation—whether it’s cold outreach, follow-ups, or data gathering—so agents can focus on closing deals.

Sounds like we are in the same boat with a handyman :) And to @Jonathan Klemm point, I have to weigh the mental capacity of handling issues remote versus spending time with family.