If you're open to looking at some resources here's what I would recommend you start with based on what you've said:1.

As a property manager, based on my conversations with our clients, below is a condensed version of what we hear most (in relation to PM in Chicago): "- Passing on the load so that you can be more present and attentive to your family (edit: and other responsibilities) and not be essentially working 24/7, on-call for the needs of tenants and property emergencies... can be worth the management fees.

We have everything microsoft so we use sharepoint to hold the files and when updated it automatically gets updated and use microsoft copilot and create a copilot agent based on those documents and internally we then have it in microsoft teams so anyone can use it.

Hey @Brett Baker, generally, any place with a great water view or directly on the water will bring more revenue.Of course profitability will all be based on purchase price and prevailing nightly rates in the area.If you find a cool 2/2 or 3/2 right on the water with a great view for 1.5m or a 2/2 or 3/2 house a block away for 600k, then I would look at the house over the condo.

house hack is possible. base way to get feet wet

Often times, there's houses or land worth $500k listed with an opening bid of $30k which is a fantastic deal; however, if you were to win the auction, there may be multiple liens and $100s of thousands of hidden fees that you have to pay at once (based on what I read online).

Please no politics here, just looking for guidance on what may happen based on your insights so I can manage my bsusiness. 

However, these programs typically qualifies borrowers based on their income, such as tax returns.The DSCR would be a good option considering you and your husband are entrepreneurs and the tax returns don't look good on paper.

I was kind of skeptical, but seems this city/town is good place for STRs based on your response.  

To remedy this for next time I am in the process of creating a design board that can be used as a base for future flips.