I think I am in scale mode and am wondering how to effectively go about doing this.

I will definitely explore the options you suggested 

If I were to buy my second property in the future, I would ideally like for it to be a duplex, triplex, quadruplex so that I can move into one of the units, rent out the others, and also rent out my first property fully.After doing more thinking and math, my other strategy is that I could go invest that $1000 into the market (which makes me a higher return than 4.875%) as well as rent out the two extra rooms that are currently not to aid in paying off my mortgage.I am wondering what y'alls thoughts are on these two strategies?

Multifamily is definitely the way to go.

Principal pay-down definitely factors into our 'return' and whether to buy at all or not.

Definitely pick a theme.

It is difficult to give a definitive answer without all of the details, but from what I gather it would be difficult to claim a loss or startup costs without closing on an investment property.

@Michelle Simoni you most definitely can, but you will need the downpayment.

@Bruce Lynn - Definitely seems like it makes the most sense for someone with a legal background or private equity.I actually believe that all businesses are similar in the fact if you are building them to scale even just a little bit they always hit a wall...this just seems like niche that needs more attention to detail and would be best for someone with a specific background in liens especially here in Chicago where we know it gets super complicated.

Detailed descriptions definitely help.