If you don't feel confident in picking your investments, most TPA's (third-party administrators, such as Fidelity or Charles Schwab) offer a pre-set list of investments based off the amount of risk you want (i.e. if you want low risk they will invest your money in a bunch of very low-risk/low-reward investments) so you don't have to worry about picking individual investments.

Bit of a pain living in a totalitarian HOA tho. 

HOA's can be a pain.

Let's say it was real heavy on education and painfully light on profit. 

Local credit union or community bank, Stay away from big banks (Chase, BAC, etc) as they are a pain in the *** to work with.

So I'm a new investor located in Michigan and I purchased my first 4plex about two months ago and one of my four tenants has been a pain on every level and I would like to hear what you guys think I should or shouldn't do in these situations.

Unless rents are painfully low it is best to wait.

If the 401k is with the current employer you probably will not be able to access those funds until you are no longer employed there (check with your plan administrator for details). 

You want to make it very painful for them to stay beyond day 3.There's the issue of damage to the property - banging into walls while moving out. 

I just got done going through the growing pains of learning how to interview and manage contractors for a project on my personal residence.