Had someone dating his daughter and they did something bad.  

I would not wait for something bad to happen.

Every now an then you will get a bad tenant (duplex or SFH).  

Prepare for the inevitable, because bad things will happen.

Two things are certain, 1) taxes are lower today than they've ever been in the past 80 years. 2) they are certain to be higher in the future.We should all be focused on paying the lowest “lifetime tax bill” not the “lowest tax bill this year”.By paying 20% and settling up my long-term capital gains is not a bad deal.

I think the big question is how badly do you want to keep the extra $50k liquid?

They look at the deal closely and won’t lend you money unless the deal makes sense, so it helps you avoid bad deals.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

How bad is the insurance, how high are the property taxes, is there an Hoa, etc etc. 

Somehow they bury bad reviews on google with great reviews.For clarity, I own DealMachine (not batchleads... totally different companies).