As long as you have reasonable expectations of:- Running a 24 hour business (mostly remote but guest communications and emergency maintenance issues)- Managing cleaners (schedule and quality)- Managing maintenance (urgent and scheduled/preventative)You will be fine.  80% of the work is remote, with the exception being cleaning and maintenance. 

flipping is exceptionally difficult. 

Around me it seems to change all the time...except almost always 1st Tuesday in Texas.As you mention though, some have monthly and some quarterly, some yearly, and plenty when they just feel like it....or have enough properties to put in the sale.

If you are asking about a JADU, the 150’ is to be used ingress/egress only   You cannot use it to push out a kitchen (except possibly if you placed a door there).JADU have even worse valuations than the poor ADU valuations due to the owner occupancy requirement for renting.  

Some banks want you to wait 6 months, others have exceptions specifically allowing you to do it before 6 are months up.

Over the last ten years, inflation has been about 3%, and I can't find appreciation numbers for Peoria that allow for a one-to-one comparison, but homes seem to have appreciated about 50% since the pandemic while holding basically steady for a few years before. https://www.zillow.com/home-values/19903/peoria-il/Maybe there's a market somewhere in the US where home price increases haven't kept pace with inflation over time, but it certainly would be an exception, and this market is not.Regarding asset protection, it's up to OP and her team to decide, but I don't think she's going to need more than a single insurance policy while just starting out.

It's sad that we treat this as exceptional behavior rather than one that is expected.

As @Tom Gimer and @Peter Walther write, why wouldn't they isure is a vital question. 

Is to be saleable and relevant the home generally needs massive upgrades to make it modern.. your not going to get top dollar for a home thats been a rental for 15 years and is as is.. ( with the exception of high priced coastal markets ) .

Now nothing can be done to the house except to bring it down.Most of these issues are things I should have identified before buying the house, had I done a thorough due diligence as most of my assumptions were wrong.The purpose of this post is to educate new and aspiring real estate investors on steps to take when New Acquisitions is involved in the sale of a house.