.: I'd be tempted into doing an STR (maybe with a higher down payment to ensure cashflow, just run ROI numbers) or an apartment complex - I personally wouldn't mess w/ small stuff.

Quote from @Jeff Sanders: Personally coming from an agent/investor in CA, I always get a quote from a broker of mine and make sure I am knowledgeable with the fees/costs.

You are going to send your wife to personally unclog that toilet.

i think this is a decision only you can make. im in a similar boat (house hacking my primary) and considering renting the whole thing out to get a solo home for myself. certainly a lot of appeal in that, given how much work goes into the house hack. but whether or not the numbers on cash flow align is up to you. personally i dont think $150 (seems like about 12%?)

Lots of loan options can close in an LLC, helocs usually need to close in your personal name.

Quote from @John Friendas: As a person with an average salary, I was wondering what the maximum amount of DSCR loans a lender would give out would look like?

I highly suggest as many in-person networking events as possible! 

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

They are all under my personal name.

I would recommend anyone lending in this environment to fix and flippers or any type of investment to be careful and get a personal guaranty and make sure person has a long track record.