If I were you I would look into the possibility of starting off with a house hack.

Since I'm taking such a cash hit, I asked the sellers agent if they would be able to designate some portion of the sale price ($200k?)

I did a search on the forums and insurance seems like it could be a major problem.I have houses in two different LLC’s in Texas and insurance is not an issue at all.

I also pay my mortgage for the house I live in.

Since house flipping has become so popular over the past few years, it's never been more critical to give your projects that extra *POP* that homebuyers will notice as they're swiping through Zillow. 

Tenant initially says it’s a new roach problem that “started when I bought the house”.

Hey @Max Smetiouk, so we have a pretty rural lake house.

In my personal opinion, it's the land that is appreciating, not the house.

For example, maybe you will get to 10, 20, 30 houses and then find an owner who has a large portfolio and all of a sudden you are at a high door count and now need to hire, need to build your policy binder, and all the other stuff that comes with running a business.

@Harish Verma You make a fair point about interest rates of late for comparing one investment against another based on the sellers’ stated cap rates.