This is the breakdown:2 tenants on month to month leases ~$250-$350 less than market1 long term tenant (15yrs) is now on month to month lease and is paying $1500 less than marketAfter consulting with a couple of people and doing some research, it sounds like anything over a I should apply banking rent raise and submit a 60 day notice (all of these units fall into that category).

If they are married/related yes, combining incomes to reach the goal is generally acceptable. 

In terms of what I learned from reading Rich Dad/Poor Dad a couple years, I think I land in the Poor Dad philosophy and I'm looking to break out of that a little, but also am risk-averse at my core. 

With $170k to deploy you most likely will have that all in one, maybe two deals, if it doesn’t go well you could end up way worse off.That said, if there are other factors like the property is a huge pain to manage or you are worried the neighborhood may actually get worse or you know you need a new roof in a couple years, then I’d consider selling.Also, even though you said it’s not a high appreciating area, do you think 1-2% is fair?

My girlfriend and I are newbies in the RE investing world, and would love to build a network with like minded couples!

They stay for a couple months without paying because they literally can’t pay. 

I think there is definitely a couple strategies at play here for you and your family. 

We will not work with anyone who has not been to Milwaukee and spent at least a couple days with us, so we can get on the same page on asset and neighborhood quality. 

Appreciation is good in TX but I’m breaking even the first couple years when I buy here.

I also don't understand why you would want to tie up your cash so long without the benefits of owning the properties.The scenario of you buying a few now and the rest in a couple years seems to be the most appealing for you both, why are you adverse to that?