I had a situation where both tenants were late on payments, and I had to go to court to evict and found the Borough to be fair on their decision.

I am in PA and yes, it is legal to charge late fees to your tenant regardless of Section 8 subsidies or not, provided the tenant's lease allows for them.

My goal is to purchase my first property between now and mid to late 2025.

Business has really gotten busy lately.

You get a Capitalization Rate (CAP Rate), which equals your annualized return by dividing the Net Operating Income (you had gross in your narrative) by the purchase price.

It's fine if you don't ever need to cancel, or have any damaged items to return but as soon as you do, their customer service feels nonexistent. 

While I do believe that some of the posters on BP are able to do a quality job self managing their portfolio of STR properties, they are spending a lot more time doing it than they’d like to admit.10 years ago in many markets STR provided outsized returns.  

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

We use RentRedi for tenant screening and management, lease documents, automated late fees, messaging, maintenance requests. 

I wish we would have started with that approach originally when we began our journey, but it's never too late to get started.