I have no problem with paying for courses, coaching, consulting, books, or any other form of valuable education. 

Supreme Court's Wayfair decision, Pennsylvania may require collection and remittance of taxes from businesses that have a substantial economic nexus in Pennsylvania"But from this site, it looks LLC needs to file Penn state tax no matter its size:https://www.revenue.pa.gov/TaxTypes/Partnerships-S-Corps-LLCs/Pages/default.aspx#:~:text=Limited%20Liability%20Companies,pay%20corporate%20net%20income%20tax."

Do they have a tax return coming that they could use to catch up? 

For other variables such as tax rates and heating costs, I find it easier to get a good evaluation.

I get the tax benefits on top of that (this is a big one for me), some small principal paydown, small monthly cashflow etc. 

appreciate you taking time to reply, that's very considerateI was going to put the property in the LLC anyway for the normal reasons - I don't think there's any harm in that for now, I'll keep consulting for the main point for what parts might look like a "sale" of the property.

Also, keep in mind that there are potential tax benefits related to investing in your primary home.

Most Jumbo lenders use IRS returns net number so be careful filing your 2023 tax return in not making the expenses total greater than 25% of income which will generally be the hit on gross rents. 

So you will need to know the rules where you work, as well as know the sales tax requirements, for where you are working.

I think this makes everything cleaner for taxes, documenting historic rental payments, and legal issues that may arise due to the barter, etc.