Technically I could line up a replacement job and let that pay the bills while I invest slowly (and that’s definitely one of my contingency plans) but in some ways that does defeat the purpose, since leaving the corporate world and focusing all of my time on an investment business is probably the biggest appeal for me.

Doesn't that defeat the process of selling it myself?

The Landlord insurance policy quotes I am receiving has a high deductible for Wind/Hail/Named Storm coverage which effectively means replacing the roof would be out of pocket for me which defeats the purpose of carrying this insurance.

Create 2 LLCs- First create an LLC in an Anonymous LLC State like Wyoming - Then create an LLC in the state I'm buying in, like Ohio- The Wyoming LLC would own the Ohio LLC - When purchasing properties, title deed would show the Ohio LLC name instead of meNegatives:California makes all tax residents register their LLCs with the State, even those formed in different states (and requires you submit the names of the owners) so this would defeat the purpose trying to stay off of public record.  

Because FHA buyers having to cover agent costs out of pocket kind of defeats the whole intent of FHA.

No lender will finance a property in another country, unless you can provide collateral from your home country or you’re a large company and the lender will give you an unsecured loan based on your balance sheet but, anyway, both options would defeat the purpose of getting leverage through the purchased property.2.

I feel like that defeats the purpose of using a VA loan then :( 

While yes it can easily be patched and mud back up, if your taking the time to hang new board, defeats the purpose when your filling holes and short cuttings with buckets of mud.

I don't know what it costs but it can't be cheap and would likely defeat the purpose.

To my knowledge, MS Word alone will allow you to create fillable forms but you still have to fill out each document individually, typing the same information repetitively, which is not only self-defeating but risks errors.