The markets are so tight each approach (in that order) requires compounding levels of time and $$$.

It's opinion based and requires market research, but in general you need to compare prices vs. market rent, size, condition, and homeownership vs. number of rentals.

There are documents that normally third parties will ask you about your 'status'If you work with a property management company, theoretically, they are suppose to withhold money on your behalf which trigues you having to file a return.You may be required to file a 1040NR which is different than the 1040 form that Citizens / Residents file.

I would need more information to truly answer these questions as there are some nuances here that require further discussion.

Some umbrella companies have switched their base insurance requirement from $300/300 to $500/500k. 

No professional is 'necessarily required' but it is normally a tradeoff between time saving, assurance that things are done correctly for a cost.For me, i can paint one of my rentals, but i decide my time is better spent elsewhere.Best of luck.

I understand that hosting in itself requires the risk of damages, would just like to know what added protection channels you guys are using.

I am not sure where to begin. with your septic and well you'll need to do site layout first with a land planner or the county. after that you'll need to check setback requirements and design plans and start budgeting with a builder. once you have a confirmed plan set and budget broken down and builder selected then you can talk to banks. most people think it starts with banks 

Understanding underwriting deals required continuous learning and adaptation to market conditions.

If you are referring to cash as in mattress money/physical cash it cannot be documented.Gift funds however, typically don't need to be sourced.