I am currently living with family, I was wanting to use my first time home buyer to purchase a multi-family for my first home and stay in a unit while renting the others to start gaining some passive income.

One of my properties, specifically 10 acre, zoned single family, is located in the mountains.

https://www.biggerpockets.com/blog/short-term-rental-loans-a...Also - PS on the advice regarding getting a vacation home loan - if this is referrring to the conventional 2nd Home / Vacation Home Loan (10% Down Loan) - I'd be very careful here, these are not supposed to be for STR investment properties (you are required to rent it out no more than half the year, not utilize prop management, ec.) - which doesn't sound like your plans for this investment

When I was looking to find a property management company to rent out my own house I wasn't getting enough value for the money IMO and I would've loved if they offered an option where they only took care of maintenance and charged a lower percentage.

Unless you already have buy & hold investors lined up make sure you have a reasonable inspection period as showing occupied properties can be a real pain unless your buyers only care about the rent & purchase price.

The security deposit is not rent.

Put 5% on the $900k SFH and rent out the $600k?

Given the location near UIC, its a good time to get students in and the general population.  

Too many arcane rent control regulations to trip you up.

They potentially getting a rental in Glastonbury, Farmington, Avon or the like town would lead to more appreciation and higher rent.