Hey Jason, You have two different situations here. 

But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

This puts both you and them in an uncomfortable situation, as you are inferring that they didn’t already price it fairly.Don’t make a list of the flaws of the property and use that to try to talk the seller down.

If you know of anyone please refer it to me.My situation is that even though I have my STR certificate the OSE officers keep knocking on my door, the 1st time I was home and I talked to them, and because I had guests they didn't insist to get in.

This will probably be the situation in 2024 and beyond.

Always good to chat with a CPA or attorney to see what fits your situation!

Do you still recommend using a real estate CPA or is their tax professionals that specialize in the more simple investor situations like mine?

@Daniel Han -  So there are essentially four parties in this situation. 

We don't rent that house  at the moment so I can't say what the current situation is.

This relative to my situation, is a super modest amount of funds.