Some months I’ve unfortunately had to pay like $150 out of pocket but I’m Planning on holding long term wise and the let the rental bare fruit later in my life because I’m only 22 and just wanted a base hit or a rental in a great neighborhood.

I would look at people that are handyman over anything else, contractors will be used to getting more money and the amount you would pay them would either be too low, or the they would not conform to your work/company.

Will definitely keep this all in mind as I move forward.

I’m going to consult a local financial planner but thought I’d ask the brilliant minds at BP as well.

They don't mind.

Especially if im paying a decent amount, i remember if they went cheap on the TP. maybe its just me.It's just you.

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

We recently did a loan involving a borrower with a mind-numbing operating agreement involving nested LLCs, retirement plans, and individuals. 

couple of bullet points to bring up:* she's on M2M* I told her on 12/7 of the new rent which would apply to a new Jan. 1 effective lease, this is when I got the "I'm moving out" message* Sent her the move-out letter on 12/11, with options for her to either be moved out by 12/31 (she's fully paid up for month of December) or by 1/11 (30 days from date of notice) and pay a pro-rated rent based on her CURRENT rent amount. her choice, either is fine with me.With all that said, I'd love to do as you mentioned and post a notice on her door. 

Buying that ugly house on a nice block will pay you handsomely in the future.