Payments that you make normally fall into one of 3 buckets100% of the payment can be factored in somewhere on the returnPartial payment can be factored somewhere on the return0% of the payment can be factored in somewhere on the returnHouse-hacking also has considerable tax implications in the event that you want to sell this property.You can potentially defer a portion or all of the gain on the investment property with 1031 exclusion.You can potentially exclude a portion or all of the gain on the personal residence with section 121 exclusion

There's a section on calculating gains/losses, and another on determining if you're eligible for an exclusion of gain (i.e. selling due to hardship like job relocation).  

If I sell my primary residence and have lived in it for only a year do I get any sort of pro rated tax benefit based on the two year capital gains exclusion.

The Umbrella does not have unique coverages/exclusions, only the Liability policy does.Example would be, the Liability policy excludes animal bites, then the Umbrella would exclude them. 

Preferably one that is exclusive in property management and not possibly dipping into it as a side hustle.

I have not heard of these being "negotiable" although admittedly do not have direct experience.I spent a few minutes trying to dig up a great BP podcast episode that was with a gentleman that deals almost exclusively with fannie/freddie non-recourse commercial loans, and touches on the penalty issues.

Wanted to add as well that there is a exclusion for seasoning requirements if you use the 'delayed financing' rule with conventional lending which allows for an immediate cash out if the property was paid for in cash.

Did you go through Zillow exclusively or did you also use a wholesaler or any other type of search? 

I've rehabbed homes all over Cleveland almost exclusively by myself and someone I enjoy company with.

For example, some hard money lenders work exclusively with commercial real estate investors.