where do I start, Outdated fuel box need to be replace, had to add a French drain due to flooding. etc etc  I think I would of been better off being my own GC doing everything myself. 

How do we protect ourselves from a tenant causing us significant damage in excess of the deposit amount? 

@Michael Plaks has a great post on this topic.2 - Assess the value of those tax deductions to you: The value of a deduction depends on (a) whether you're actually able to use it to reduce taxable income and (b) your marginal tax rate.As an STR, assuming the average rental period is 7 days or less, key items to consider are: (a) material participation and (b) avoidance of "excessive" personal use.

Lower demand and excess of investment properties. 

I would guess in the near future you'll start to see meters that automatically shut-off after excessive use.

When a tenant moves out, transfer the deposit back to Checking so it's ready to apply towards expenses or refund the Tenant.If you end up with excess funds in the Checking account, I recommend you transfer it to a third account designated explicitly for future investments.

Any voids, ridges, or gaps under the LVP will lead to excess movement and splitting at the tongue/groove or click-lock joints. 

The drawback you have to fit "in the box"; 20% down +, excessive reserves requirement, specific restrictions on tradelines, assets guidelines, DTI under 43%, owner occupancy etc.. if you are open to ARMs you will have a bit more options..Also need to consider the type of property - if condo/condotel banks might not finance at all.. there are many factors to consider we do have some good outlets for jumbo, would be happy to review your scenario and give you a quote.

The larger brokerages are usually too prohibitive and costly, lots of oversight and charging a lot of excess fees in addition to hefty commission split.

Your excessive use of ALL CAPS shows your overly emotional investment to a very low stakes situation.