Outside of real estate, I enjoy spending time with family.  

Buy a property when it feels good is when you are buying your primary home where your kids will grow up and you'll live with your family.

He's helping me to narrow down a potential multi-family property that I will be house hacking, (the deadline I have given myself to be in it is May).

But I wouldn’t be focused on a multifamily in your situation as they are pretty rare to find in an entry-level price point in this area and if they are under ~$1M it’s probably going to be in bad condition or in a bad location (with some exceptions of course, but harder to find that a single family home in a good location that will appreciate better). 

When I worked with a property management company, we had someone buy a unit (single family) that had a STR and marketed it as a STR.

1st tenant (that came with the house)- she is a Section 8 tenant and clearly knows the game better than me hence the prolonged delayed Marshall’s execution.I cannot have 2 Government assistance programs in the property at the same time since it is not a legal 2 family.

if you want to buy a vacation house for your family, and you can afford it, and you'll occasionally rent it out - that's great, it's just not an investment. 

. - Family: Kids? 

For our last single family residence we had a young married couple move in with a brother, all three applied.  

., "I will buy at least one single-family home, duplex, triplex, or fourplex before the end of 2019") and then do it.