@Evan Polaski yes the cash that I’ve allocated is going into low volatility liquid securities that also generate some yield.  

One strategy for acquiring a coastal vacation property or future primary can be to secure and operate the property as a mid or short term rental to help sustain or offset the investment.

By securing long-term tenants and maintaining the property’s condition, I’ve enjoyed consistent rental income and significant appreciation in property value.

For those landlords who take security deposits in City of Chicago, is a separate business bank account sufficient for the security deposit or do I still need to set up the special landlord account that requires all W-9 paperwork from tenants etc?

How would you handle this in the security deposit?

I would recommend only using a short or mid-term rental house hack for a 2-4 unit property or a house with a detached ADU for your security and the comfort of the guests, which will make it more profitable.

I made the mistake of empathizing, let them have keys before the full security deposit was paid.

Partnering with experienced investors can provide valuable insights.5.Creative Financing:Explore creative financing options like seller financing or private lenders to secure better terms.6.Rent by the Bedroom:In high-demand areas, renting by the bedroom can boost your rental income significantly.7.Local Market Analysis:Stay updated on local market trends and network with other investors for insights and opportunities.Always analyze potential investments thoroughly and run detailed cash flow projections.

Regardless of situation you should be aware of all lease terms of current tenants, security deposits, tenant contact info, pets, rental rates, etc. 

i  would say househacking in expensive area is the best strategy.I got all tenants paying my mortgage , i never met them and they made the house more secured as well because there's always people in the house.