The #1 reason that landlords fail is due to failure to manage to the lease (Source: American Apartment Owners' Assn). 

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

This might give a one-time (non-scalable) boost to cash flow, offer multiple value-add options, and allow the house-hacker peace of mind, via the assumed mortgage, in long-term breakeven or positive cash flow in the event that the value-add plans end up not being executed, and/or the person has to move out, and rent by the room or STR become unavailable for some reason at a future date.

Having reasonable expectations, hiring a local professional (Realtor or PM), doing your research, and doing everything right (i.e. pro photos, professional design, good renovation, proper amenities and location, etc) are the keys to success in 2025.

I like umbrella because there is no worry of being pierced for inadequate separation of finances, if sued you have a heavy weight in your corner who has all the consequences of a defeat, and because usually it is reasonably priced (mine today is not so reasonably priced but I believe it is mostly related to the risks of CA).I do understand that the probability of needing the umbrella policy is low.  

Reason is a Heloc generally carries a higher rate on a shorter term and "Can Never" be used as an "Asset, or for PITI reserves" which are both required when you buy an investment property. 

They're hiring PMs for a reason and they fire them for not maximizing cash flow.  

In your market it is difficult to find mulit family RE that was recently built and reasonably priced. 

Speaking of, one of the reasons why they're behind is because of debt coming due later this year.

FHA will not use any short term rental data.Something else to think about - any reason why you wouldn't use a Fannie Mae loan here?