Chicagoland is extremely tenant friendly so understand that going in. 

FYI I do have plenty of reserves for my other units already, but would like to keep each property separate.My question is, where should I draw funds from to pay the least amount in penalties, taxes, loan interest, etc. from the following sources I have available:- 20 year 401k loan for a property- Sell a piece of my stock portfolio at 15% capital gains tax- Take a HELOC against an existing property- Private money loan from a trusted partner I have worked with beforeAlternatively, I could pool the reserves for all my properties to ensure I can cover anything immediate and know that I could always sell off a piece of my stock portfolio if needed and have the funds within 3 business days or set up a HELOC and only draw from it if needed.Appreciate any thoughts or what you have done in the past.

I absolutely understand your point.

It’s not just about luxury anymore; it’s about creating spaces that adapt to the future and the people living in them.For investors, understanding these shifts is key.

Does it mean something I am not understanding?

Here’s some context: Property 1: >$100k in EquityValue: $325kDebt: $220k @ 2.88% (30-year fixed)Property 2: >$70k in EquityValue: $325kDebt: $252k @ 3.38% (30-year fixed)Extra considerations: - I have $15-20k liquid to use for any of these deals- My current job is relatively stable, but not high-payin- Current properties in TX, living in NY, looking to invest in Mid-West (crazy, I know)- No other debt obligations besides the two mortgagesUltimate goal/timeline: Though a bit ambitious, I’d love to build up the portfolio to 10-20 units in the next two yearsI understand that any/all replies aren't financial advice; all ideas welcome for information purposes. 

That being said it’s worth understanding what’s working locally as your next step varies jurisdiction to jurisdiction.

Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

Aside from strategy you must understand how to underwrite a deal. 

I understand that with traditional mortgages, it is unlikely to receive lending that incorporates speculative renovation costs.