If possible, not use an agent, to lower commission owed expense (not sure if this is possible in Chicago, IL).

It'll be more expensive than normal loans because it is mixed use. 

Thank you so much guys.Best,Jake Before dumping $500k into an asset, maybe consider something smaller and spending like $50k or $100k on a less expensive property.

Thank you - Shant For me personally, I am not too much concerned with putting each property in its own LLC as that can get expensive.

I managed the properties myself to keep the expenses down.

78k of expenses with mortgage and only 65k of estimated income? 

We agree we have 50/50 liability for expenses in the case of a loss.We differ in terms of cash flow breakdown.

Most Jumbo lenders use IRS returns net number so be careful filing your 2023 tax return in not making the expenses total greater than 25% of income which will generally be the hit on gross rents. 

It sounds like you want to be a rental property owner/investor and not just looking to minimize your out of pocket housing expenses (getting a roommate to help cover your mortgage with a single family home).  

Private money can be expensive; it would be best to have an exit strategy.