I find that most arbitrage "naysayers" have not done rental arbitrage and are afraid of the risks, all of which can be mitigated (with simple contracts, sublet & lease termination agreements, STR insurance, etc.)I have been growing a 25-unit rental arbitrage & furnished rental business for the past 3 years in and around San Francisco since I left a 25-year career in corporate America. 

4%, 5%  I want incorporate all the planned and actual expenses for the property when I am reviewing the underwriting. 

It is best practice to incorporate repairs into your underwriting.4.

I will say this though...if you can get a duplex or triplex up there, you can incorporate long term for  one or two of the units, while leaving one unit as a short term or personal use.

My property managers are all incorporated so its my understanding that no 1099 misc needs to be issued by me to them for their monthly retained fee, they in turn do issue 1099s to all unincorporated independent contractors that perform work on my properties.So even though I do claim 199A QBI benefits for all my Rental Real Estate activities (as they satisfy the 162 trade or business standard), I assume there is still no requirement that I file a 1099 Misc as I make no payments to unincorporated independent contractors?

My final point is management fees - does that incorporate that tenant placement fee estimates?

For example the wind blows the pool chairs so they look a bit messy.

SEO + Credibility.It is the credibility term that incorporates bringing value to your traffic.Yes my system works.

I basically look at the competitors that are performing well to see what they’re doing right, find the average word count, recommend some keywords and phrases to incorporate, and then structure an outline for the writer to go off of.

It sounds like you have the last item incorporated in your plan.