Many owners look at their day jobs to figure out how much their time is worth and then decide to hire someone that charges less and has more experience. 

You'll get random advice from a bunch of us armchair lawyers here, but that's worth exactly what you pay for it. 

For example I have one property in the lower price point as a rental (triplex that is now worth around $225K).

@Mike Clary Agree- tax issues are hyper local, which is why I said it wasn't worth it in my case. 

You are heading into a busy season, so if you are priced at or near similar rents, then may be worth waiting longer as market is just getting stronger. 

I've encountered several situations where tenants not only broke their lease but also caused damages, sometimes even leaving before the lease ended with damages behind.To clarify, when I mention damages, I'm not talking about normal wear and tear but rather significant repairs costing between $5,000 to $8,000, which don't qualify as vandalism for insurance purposes.In the past, property managers I've spoken to have often discouraged pursuing tenants for these damages, citing it as not worth the effort.Here are my questions for you:- Would you pursue the tenant?

However I also think spending a few bucks to help mitigate that risk is worth it to me.

You will have to google it: I saw them but can't remember what their name was. 

Is it worth paying the penalty?

It was worth it and I really appreciate it.