So, I'd rather that the wholesaler assigned the contract to my flipping LLC so that it falls under my existing operation...I hope that makes sense. 

If you're going the umbrella insurance route, make sure it will cover you for several things including just the routine slip and fall (like mold or earthquake).

Should I wait to see if the housing market will fall?

When you BRRR the property, you rent it , you do not sell it , your rental income after expenses is subject to ordinary income tax but not considered self-employment tax.Scenario 3: ( Which is the scenario you fall under) Your cash-out refinance is considered borrowed money from the bank and can not be taxed.  

I have started looking in Southeast Idaho (Pocatello, Blackfoot, Idaho Falls and Rexburg) but haven't found anything yet. 

As a new RE investor, I don't really have the proper tools to analyze this decision, other than thinking that the potential upside of renting is small compared to the potential downsides of a RE crash, future vacancy between tenants, falling rental prices, falling home prices, etc.

Houston-area apartment rents continue to fall amid COVID-19 in May"Houston-area apartments saw another month of declining average rents in May, a month that is usually in the midst of an annual upswing in the industry, driven by an exodus of renters."   

Currently starting a job in Seattle remote from Milwaukee but will likely move to Seattle in the early fall.

As for vetting buyers, many brokers screw up co-op board packages, so it's not uncommon for FSBO co-op deals to fall apart or end up with board turn downs based on things that could have been flagged early on. 

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 exclusionThe answer to your $10,000 question is it depends on if the unit is in service and what the breakdown of the $10,000 is(repair vs improvement) and if there is any safe harbor/election to currently expense the items.